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Structure-activity relationship of antibacterial bio-based epoxy polymers made from phenolic branched fatty acids
Progress in Organic Coatings ( IF 6.6 ) Pub Date : 2021-03-16 , DOI: 10.1016/j.porgcoat.2021.106228
Kun Huang , Xuetong Fan , Richard Ashby , Helen Ngo

In order to study the structure-activity relationship of antibacterial bio-based epoxy polymers made from phenolic branched fatty acids (phenolic BCFAs), a series of curing agents (i.e., phenolic BCFA-amides (phenolic BCFAAs)) were prepared from phenolic BCFAs and polyamines at 90 ℃ and 160 ℃. Those phenolic BCFAs were made from phenol, thymol, carvacrol, and creosote, respectively, while the polyamines were ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and hexamethylenediamine (HDA). The prepared curing agents were then used to make different antimicrobial bio-epoxy polymers with a commercial epoxy resin, diglycidyl ether of bisphenol A (DGEBA). All the monomers were thoroughly characterized by Fourier-transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR). Two bio-epoxy polymers, phenol-BCFA (EDA) and creosote BCFA (EDA), were found to be most active against both Gram-positive and Gram-negative bacteria. The leaching experiments on the phenol-BCFA (EDA) showed no signs of small molecules (i.e., biocides) leaking out of the polymer to inactivate the bacteria. Most importantly, the reusability study indicated that the polymer was inherently antibacterial and maintained its efficacy for at least three uses. This study presents important findings on the antimicrobial activity of individual phenolics, polyamines and molecular weights of the curing agents, and the evidence demonstrates that the amphiphilicity contributes to the key impact of the antimicrobial activity of the bio-epoxy polymers.



中文翻译:

酚类支链脂肪酸制备的抗菌生物基环氧聚合物的构效关系

为了研究由酚支链脂肪酸(酚BCFA)制得的抗菌生物基环氧聚合物的构效关系,一系列固化剂(在90℃和160℃下由酚BCFA和多胺制备酚BCFA-酰胺(酚BCFAA)。这些酚类BCFA分别由苯酚,百里香酚,香芹酚和杂酚油制成,而多胺为乙二胺(EDA),二亚乙基三胺(DETA),三亚乙基四胺(TETA),四亚乙基五胺(TEPA)和六亚甲基二胺(HDA)。然后将制备的固化剂用于与商业环氧树脂双酚A的二缩水甘油醚(DGEBA)制备不同的抗菌生物环氧聚合物。所有单体均通过傅里叶变换红外光谱(FT-IR)和核磁共振光谱(NMR)进行了全面表征。发现两种生物环氧聚合物酚-BCFA(EDA)和杂酚BCFA(EDA)对革兰氏阳性菌和革兰氏阴性菌均最具活性。(例如,杀生物剂)从聚合物中泄漏出来使细菌失活。最重要的是,可重复使用性研究表明该聚合物具有固有的抗菌作用,并且至少在三种用途中均保持了其功效。这项研究提出了有关单个酚类,多胺和固化剂分子量的重要抗微生物活性的发现,证据表明两亲性对生物环氧聚合物的抗微生物活性起关键作用。

更新日期:2021-03-16
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