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Stabilization Mechanism of a Black Leuco-Developer System and Its Tinctorial Strength as Viewed from the Crystal Structure

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Certain leuco dyestuffs are known to exhibit a brilliant color by reaction with a phenolic developer; 2-[(4-hydro-xyphenyl)sulfonyl]-phenol (BPS) is a well-known developer for black leuco dyes such as 6'-(diethylamino)-3'-methyl-2'-(phenylamino)-spiro[isobenzofuran-1(3H), 9'-[9H]-xanhen]-3-one (ODB) in thermosensitive papers. Although BPS is a small molecule (molecular weight: about 250), it is thermally stable as characterized by a high melting point of about 184°C. Furthermore, the stability of BPS is also extended to the 1:1 "leuco/developer" system. In this connection, structure analysis of BPS has been carried out in order to elucidate the stability of BPS itself as well as its leuco/developer system. Then, we found that one BPS molecule is hydrogen bonded to four different neighboring ones, forming an OH···O two-dimensional hydrogen-bond network. This ensures a high thermal stability of BPS. On the other hand, in the ODB/BPS system, only one of the four hydrogen bonds in BPS is used for the formation of the 1:1 ODB/BPS colorant while the remaining three hydrogen bonds keep the network. As for the tinctorial strength in spin-coated ODB/BPS, the color intensity is found to be limited to about 70% of the maximum available value. This is because there is a fraction of ODB molecules, whose lactone ring is still closed owing to the steric hindrance.
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Document Type: Research Article

Affiliations: Graduate School of Engineering, Yokohama National University, 240-8501 Yokohama, Japan

Publication date: 2010-03-01

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  • The Journal of Imaging Science and Technology (JIST) is dedicated to the advancement of imaging science knowledge, the practical applications of such knowledge, and how imaging science relates to other fields of study. The pages of this journal are open to reports of new theoretical or experimental results, and to comprehensive reviews. Only original manuscripts that have not been previously published, nor currently submitted for publication elsewhere, should be submitted.

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