Color Development Mechanism of Urea–Urethane Developers for High-Performance Thermo-Sensitive Paper

A series of compounds with both urea and urethane moieties have been developed as color developers for high-performance thermo-sensitive paper. The compounds have lower environmental loads than conventional phenolic developers. They were also found to greatly improve the speed of the printed images. In this study, we studied the coloring mechanism of the compounds when used as developers for a fluoran dye, and we investigated the stability of the colored solid state. The urea–urethane compounds were found to form black amorphous solids with the fluoran dye. Infrared (IR) measurements of the black solids, based on six urea–urethane derivatives, revealed that the colored dye has a ring-opened structure in a carboxylic acid form and that the urea group works as a proton donor for the ring-opening reaction. The stability of the black amorphous solids was also evaluated using thermal analysis and molecular orbital calculations in addition to IR data. The results indicate that the number of urea–urethane units and the planarity of the urea moiety are important parameters for the stability of the colored solid state.