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Phenolic fatty acid-based epoxy curing agent for antimicrobial epoxy polymers
Progress in Organic Coatings ( IF 6.6 ) Pub Date : 2020-04-01 , DOI: 10.1016/j.porgcoat.2019.105536
Kun Huang , Richard Ashby , Xuetong Fan , Robert A. Moreau , Gary D. Strahan , Alberto Nuñez , Helen Ngo

Abstract Epoxy resins are one class of important reactive pre-polymers used in the coating industry. To manufacture epoxy resins with antimicrobial properties, active quaternary ammonium groups are often introduced into the polymeric backbones following resin polymerization reactions for structure modification. However, these complicated approaches associated with these types of reactions make the commercialization of the antimicrobial epoxy polymers uneconomical, impractical and inconvenient. Besides, quaternary ammonium groups are undesirable because the hydrophilicity of the groups makes the resins less water-resistant. In order to simplify the development of antimicrobial epoxy polymers, we prepared an amide by reacting novel bio-based phenolic-branched fatty acids with ethylenediamine. The resulting amide was cured into a commercial epoxy resin -- diglycidyl ether of bisphenol A (DGEBA), which was solution-cast into epoxy polymer films. The antimicrobial activities of the resulting epoxy polymer films were investigated. The crude phenolic branched fatty acid amides (PBC-FAAs) as curing agents were separated and characterized by thin-layer chromatography, proton nuclear magnetic resonance (1H-NMR), gas chromatography-mass spectrometry (GC MS), liquid chromatography-mass spectrometry (LC/MS) and Fourier-transform infrared spectroscopy (FT-IR). The thermal and mechanical properties of the polymer films were also investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and dynamic mechanical analysis (DMA). Cured epoxy films prepared from purified PBC-FAA exhibited antimicrobial activity against Listeria innocua. However, the crude, unpurified PBC-FAA-cured epoxy film showed much more promising antimicrobial activity against both Listeria innocua (Gram positive) and Escherichia coli (Gram negative).

中文翻译:

酚类脂肪酸基环氧固化剂,用于抗菌环氧聚合物

摘要 环氧树脂是涂料工业中使用的一类重要的反应性预聚物。为了制造具有抗菌性能的环氧树脂,通常在树脂聚合反应后将活性季铵基团引入聚合物主链中以进行结构改性。然而,与这些类型的反应相关的这些复杂方法使得抗微生物环氧聚合物的商业化不经济、不切实际且不方便。此外,季铵基团是不可取的,因为这些基团的亲水性使树脂的防水性较差。为了简化抗菌环氧聚合物的开发,我们通过将新型生物基酚支化脂肪酸与乙二胺反应制备了一种酰胺。将所得酰胺固化成商品环氧树脂——双酚 A 的二缩水甘油醚 (DGEBA),然后将其溶液浇铸成环氧聚合物薄膜。研究了所得环氧聚合物膜的抗微生物活性。采用薄层色谱法、质子核磁共振(1H-NMR)、气相色谱-质谱(GC-MS)、液相色谱-质谱法对作为固化剂的粗酚支化脂肪酸酰胺(PBC-FAAs)进行分离和表征(LC/MS) 和傅里叶变换红外光谱 (FT-IR)。还通过差示扫描量热法 (DSC)、热重分析 (TGA) 和动态力学分析 (DMA) 研究了聚合物薄膜的热性能和机械性能。由纯化的 PBC-FAA 制备的固化环氧薄膜表现出对无害李斯特菌的抗菌活性。然而,未经纯化的 PBC-FAA 固化环氧膜对无害李斯特菌(革兰氏阳性)和大肠杆菌(革兰氏阴性)显示出更有前景的抗菌活性。
更新日期:2020-04-01
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