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

    抄録

    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.

    本文言語英語
    ページ(範囲)549-555
    ページ数7
    ジャーナルDyes and Pigments
    139
    DOI
    ジャーナル掲載日出版済み - 2017 4 1

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    Derivatives
    Hydrogen bonds
    Color
    Molecules
    Melting point
    Crystal structure
    Crystalline materials

    Keywords

      ASJC Scopus subject areas

      • Chemical Engineering(all)
      • Process Chemistry and Technology

      これを引用

      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.

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

      研究成果: ジャーナルへの寄稿記事

      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, 巻 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 4 1;139:549-555. 利用可能場所, 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.

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

      研究成果: ジャーナルへの寄稿記事

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      author = "Saori Gontani and Tatsuya Ohashi and Kyohei Miyanaga and Takaaki Kurata and Yoshiki Akatani and Shinya Matsumoto",
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      AU - Miyanaga,Kyohei

      AU - Kurata,Takaaki

      AU - Akatani,Yoshiki

      AU - Matsumoto,Shinya

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      N2 - 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.

      AB - 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.

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      KW - Fluoran dye

      KW - Hydrogen bonding network

      KW - Thermal paper

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