Department of Applied Chemistry, College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, PR China.
Department of Applied Chemistry, College of Chemical and Biological Engineering, Shandong University of Science and Technology, Qingdao 266590, PR China.
Int J Biol Macromol. 2020 Jul 1;154:173-181. doi: 10.1016/j.ijbiomac.2020.03.117. Epub 2020 Mar 16.
A silane unit with enhanced synergism that is realized using one cationic quaternary ammonium salt (QAS) to draw anionic bacteria to two N-halamine functionalities was designed and polymerized on cellulose for superior biocidability. A monomer containing one tertiary amine, one amide N-H, and one imide N-H, was synthesized via alcoholysis of 3-triethoxysilylpropyl succinic anhydride with 2-(dimethylamino)ethan-1-ol and following esterification with 5-(4-hydroxyphenyl)hydantoin. The triethoxysilyl groups of the monomer were hydrolyzed to silanol groups to condense with counterparts in different hydrolyzates and with hydroxyl groups on cellulose to form a polymeric modifier. Each silane unit of the modifier has one QAS and two N-halamine functionalities (quat/di-N-halamines) after quaternization of the tertiary amine and chlorination of the amide and imide hydrogens. The resultant cellulose suppressed (7 logs) both Staphylococcus aureus and Escherichia coli within 3 min, demonstrating an enhanced synergism since the inactivation rate is faster than counterparts decorated with only N-halamine and with synergistic units of one cationic center and one N-halamine. The modifier exhibited promising stability and rechargeability toward washings, UV irradiation, and long-term storage. The proved enhanced synergism from the integration of one cationic center with multiple N-halamines directs the synthesis of more powerful biocides for developing antibacterial polymers.
设计并将一种带有增强协同作用的硅烷单元聚合到纤维素上，用于优异的杀菌能力，该硅烷单元使用一种阳离子季铵盐 (QAS) 将阴离子细菌吸引到两个 N-卤胺官能团上。通过 3-三乙氧基硅丙基琥珀酸酐与 2-（二甲氨基）乙-1-醇的醇解以及随后与 5-（4-羟基苯基）海因的酯化，合成了一种含有一个叔胺、一个酰胺 N-H 和一个酰亚胺 N-H 的单体。单体的三乙氧基硅烷基水解为硅醇基，与不同水解物中的对应物以及纤维素上的羟基缩合，形成聚合改性剂。改性剂的每个硅烷单元在叔胺季铵化和酰胺及酰亚胺氢的氯化后，具有一个 QAS 和两个 N-卤胺官能团（季铵/二 N-卤胺）。所得纤维素在 3 分钟内抑制了金黄色葡萄球菌和大肠杆菌（7 对数），表现出增强的协同作用，因为失活速率比仅用 N-卤胺和一个阳离子中心与一个 N-卤胺的协同单元修饰的对照物更快。该改性剂在洗涤、UV 照射和长期储存方面表现出良好的稳定性和可再充电性。将一个阳离子中心与多个 N-卤胺结合的协同作用的证明为开发抗菌聚合物指导了更强大杀菌剂的合成。
