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Mechanistic Insights into Oxidative Oligomerization of p-Phenylenediamine and Resorcinol
Aaron D Bailey1,2, Bryan P Murphy1, Hairong Guan2
1The Procter & Gamble Company, 8700 Mason-Montgomery Road, Mason, Ohio 45040, United States.
Abstract:
An efficient synthesis of a green dye from oxidative coupling of p-phenylenediamine (PPD) and resorcinol (in a 2:1 ratio) has been developed. Reactivity studies of this dye molecule with a variety of reagents (PPD, resorcinol, the oxidized form of the green dye itself, and a dinuclear indo dye) demonstrate that it cannot be the key reactive intermediate in reported oxidative oligomerization of PPD and resorcinol. However, the trinuclear species does form large aggregates. At least one viable pathway of oligomerization has been demonstrated with the dinuclear indo dye.
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