Development of Unimolecular Thermo-Response Dyes and Application to the Image Formation

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Fluoran dyes are widely used as pressure-and heat-sensitive dyes for carbonless paper and paper for fax systems. Coloration occurs when the dyes react with acid, normally phenolic compounds, upon heating. To retain the colorless form before heating, the dyes must be protected from contact with acid. This often causes technical problems and restricts the use of organic medium such as polymer films. Our strategy utilized the fact that upon heating, neutral allyl aryl ethers generate acidic phenol groups by the Claisen rearrangement. Phenol groups thus generated undergo intramolecular acid-base reaction, which in turn causes the ring opening of the lactone groups and the coloration.In this project, we investigated the development of the unimolecular thermo-response dyes and application of the dyes to Image formation. The main results obtained in the project are briefly outlined below :1. Various unimolecular theromo-response dyes were synthesized aiming at the development of the color variation for the dyes.2. Syntheic scheme for the dyes were modified for the large-scale preparation.3. Test papers for the dyes were prepared.4. X-ray analyzes of the dyes (before and after the coloration) were performed.5. Characteristics of the dyes were carried out by several spectroscopic methods.6. Molecular design and syntheses of unimolecular light-response dyes were studied.