Tunicate-Inspired Gallol Polymers for Underwater Adhesive: A Comparative Study of Catechol and Gallol,Biomacromolecules

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Tunicate-Inspired Gallol Polymers for Underwater Adhesive: A Comparative Study of Catechol and Gallol
Biomacromolecules ( IF 5.5 ) Pub Date : 2017-08-30 00:00:00 , DOI: 10.1021/acs.biomac.7b00921
Kan Zhan ₁ , Chaehoon Kim ₁ , Kyungmo Sung ₁ , Hirotaka Ejima ₂ , Naoko Yoshie ₁

Affiliation

Man-made glues often fail to stick in wet environments because of hydration-induced softening and dissolution. The wound healing process of a tunicate inspired the synthesis of gallol-functionalized copolymers as underwater adhesive. Copolymers bearing three types of phenolic groups, namely, phenol, catechol, and gallol, were synthesized via the methoxymethyl protection/deprotection route. Surprisingly, the newly synthesized copolymers bearing gallol groups exhibited stronger adhesive performances (typically 7× stronger in water) than the widely used catechol-functionalized copolymers under all tested conditions (in air, water, seawater, or phosphate-buffered saline solution). The higher binding strength was ascribed to the tridentate-related interfacial interaction and chemical cross-linking. Moreover, gallol-functionalized copolymers adhered to all tested surfaces including plastic, glass, metal, and biological material. In seawater, the performance of gallol-functionalized copolymer even exceeds the commercially available isocyanate-based glue. The insights from this study are expected to help in the design of biomimetic materials containing gallol groups that may be utilized as potential bioadhesives and for other applications. The results from such a kind of comparable study among phenol, catechol, and gallol suggests that tridentate structure should be better than bidentate structure for bonding to the surface.

中文翻译：

胶体启发的用于水下胶粘剂的Gallol聚合物：邻苯二酚和Gallol的比较研究

由于水合作用引起的软化和溶解作用，人造胶通常无法在潮湿的环境中粘附。被膜的伤口愈合过程激发了以胆甾醇官能化的共聚物作为水下粘合剂的合成方法。通过甲氧基甲基保护/脱保护途径合成具有三种酚基的共聚物，即酚，邻苯二酚和没食子醇。出人意料的是，在所有测试条件下（在空气，水，海水或磷酸盐缓冲的盐溶液中），新合成的带有胆醇基团的共聚物表现出比广泛使用的邻苯二酚官能化的共聚物更强的粘合性能（在水中通常增强7倍）。较高的结合强度归因于三齿相关的界面相互作用和化学交联。而且，胆甾醇官能化的共聚物粘附到所有测试的表面，包括塑料，玻璃，金属和生物材料。在海水中，基于胆甾醇官能化的共聚物的性能甚至超过了市售的基于异氰酸酯的胶水。预期该研究的见识将有助于设计包含没食子醇基团的仿生材料，这些材料可用作潜在的生物粘合剂和用于其他用途。这种在苯酚，儿茶酚和没食子醇中进行的可比性研究的结果表明，三齿结构应比双齿结构更好地键合到表面上。预期该研究的见识将有助于设计包含没食子醇基团的仿生材料，这些材料可用作潜在的生物粘合剂和用于其他用途。这种在苯酚，儿茶酚和没食子醇中进行的可比性研究的结果表明，三齿结构应比双齿结构更好地键合到表面上。预期该研究的见识将有助于设计包含没食子醇基团的仿生材料，这些材料可用作潜在的生物粘合剂和用于其他用途。这种在苯酚，儿茶酚和没食子醇中进行的可比性研究的结果表明，三齿结构应比双齿结构更好地键合到表面上。

更新日期：2017-08-30

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