Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper

Saori Gontani, Tatsuya Ohashi, Kyohei Miyanaga, Takaaki Kurata, Yoshiki Akatani, Shinya Matsumoto

    Abstract

    The crystal structure of a new bisphenol S derivative, 3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone was analyzed. This compound is used as colour developer in high-performance thermal paper, because of its high colour sensitivity and excellent image stability. In the crystalline phase, each molecule of this derivative is linked to four neighbouring molecules by O[sbnd]H⋯O[dbnd]S intermolecular hydrogen bonds. In order to understand the solid-state properties of the new derivative, its hydrogen bonding features were compared to those of the parent bisphenol S compound. The hydrogen bonding network of the new derivative forms two-dimensional square lattice sheets stacked along the b axis. This stacking arrangement, which is different from that of the unsubstituted compound, results in a lower number of hydrogen bonds per unit volume. This structural feature was considered to be correlated with the considerably lower melting point of the new derivative compared to that of the unsubstituted one. This property would result in a good coloration sensitivity of the new derivative when used as colour developer.

    Original languageEnglish
    Pages (from-to)549-555
    Number of pages7
    JournalDyes and Pigments
    Volume139
    DOIs
    StatePublished - 2017 Apr 1

    Fingerprint

    Derivatives
    Hydrogen bonds
    Color
    Molecules
    Melting point
    Crystal structure
    Crystalline materials

    Keywords

    • Bisphenol S
    • Colour developer
    • Crystal structure
    • Fluoran dye
    • Hydrogen bonding network
    • Thermal paper

    ASJC Scopus subject areas

    • Chemical Engineering(all)
    • Process Chemistry and Technology

    Cite this

    Gontani, S., Ohashi, T., Miyanaga, K., Kurata, T., Akatani, Y., & Matsumoto, S. (2017). Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper. Dyes and Pigments, 139, 549-555. DOI: 10.1016/j.dyepig.2016.12.049

    Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper. / Gontani, Saori; Ohashi, Tatsuya; Miyanaga, Kyohei; Kurata, Takaaki; Akatani, Yoshiki; Matsumoto, Shinya.

    In: Dyes and Pigments, Vol. 139, 01.04.2017, p. 549-555.

    Research output: Contribution to journalArticle

    Gontani, S, Ohashi, T, Miyanaga, K, Kurata, T, Akatani, Y & Matsumoto, S 2017, 'Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper' Dyes and Pigments, vol 139, pp. 549-555. DOI: 10.1016/j.dyepig.2016.12.049
    Gontani S, Ohashi T, Miyanaga K, Kurata T, Akatani Y, Matsumoto S. Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper. Dyes and Pigments. 2017 Apr 1;139:549-555. Available from, DOI: 10.1016/j.dyepig.2016.12.049

    Gontani, Saori; Ohashi, Tatsuya; Miyanaga, Kyohei; Kurata, Takaaki; Akatani, Yoshiki; Matsumoto, Shinya / Structural comparison of two bisphenol S derivatives used as colour developers in high-performance thermal paper.

    In: Dyes and Pigments, Vol. 139, 01.04.2017, p. 549-555.

    Research output: Contribution to journalArticle

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