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摘要本论文中制备了一种同时具有防止细菌黏附和灭菌性能的两性离子单体。以水杨酸为最初原料，以溴乙酰溴为酰化试剂完成对水杨酸羟基氧上的酰化。再以叔丁醇与第一步反应生成的水杨酸衍生物上的羧基发生酯化反应，保护羧基。然后用含碳碳双键的叔胺与上步反应产物发生卤代烃的亲核取代反应，生成了季铵盐类型的两性离子单体。最后利用盐酸催化酯键水解，使最初的水杨酸上的羧基游离出来。 最终合成了通过可水解的酯键连接抗菌离去基团水杨酸 SA偶合羧基甜菜碱 CB的两性离子单元。 通过1H NMR 和 FTIR 确定了目标产物抗菌单体的结构。由于此单体含有双键，可以通过化学引发的方法，将单体制成两性离子水凝胶。并以金黄色葡萄球菌和大肠杆菌为试验菌，研究了此种水凝胶的杀菌性能，在 9h时能达到 99.1%的E.coli杀菌率和98.2%的S.aureus杀菌率。以导入荧光蛋白的大肠杆菌为试验菌，通过荧光显微镜观察水凝胶上细菌吸附情况，确定了其抗细菌黏附性能。研究表明，与对照样品相比，制备的两性离子水凝胶材料表现出了优异的抗细菌黏附性能和杀菌性能。表明该种水凝胶具有更加优良与持久的抗黏附和灭菌效果。 21597
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关键词 双重抗菌 两性离子水凝胶 抗细菌黏附性能 杀菌性能
Title Preparation and application of polymerizable antibacterial
monomer with dual antibacterial action
Abstract
In this paper ,A kind of both prevent bacterial adhesion and sterilization performance
zwitterionic monomer was synthesized. With salicylic acid as initial raw materials, with
bromoacetyl bromide as the acylating reagent complete acylation of salicylic acid on
hydroxyl oxygen. Again with tertiary butyl alcohol with the first step carboxyl acid of
salicylic acid derivatives form esterification reaction to protect the carboxyl. Then use
carbon-carbon double bond of tertiary amine and the halogenated hydrocarbon forming
nucleophilic substitution reaction and generating quaternary ammonium salt type
zwitterionic monomer. Use hydrochloric acid catalyze the hydrolysis of ester bond to
make the original salicylic acid on the carboxyl freed. Finally a hydrolyzable ester
linkages with antibacterial leaving group comprising salicylic acid SA coupling
carboxy betaine zwitterionic units was synthesized. The monomer contains an
unsaturated double bond that allows it to polymerize by chemical initiation, The
monomer was made to zwitterionic hydrogel. The obtained monomer was
characterized by 1
H-NMR and FTIR spectra. The antimicrobial activity of the hydrogel
was investigated against both E.coli and S.aureus. The hydrogel killed above 99.1% E.
coli and above 98.2% S. aureus after contact 9 h. And the antifouling efficacy was
investigated against E.coli which contained the fluorescent protein. Compared to the
samples, the hydrogel exhibited excellent antifouling and antimicrobial properties.
Through comparing anti-adhesion properties and antibacterial effect, it indicate the
hydrogel have more excellent and long-lasting anti-adhesion and sterilization effect.
Keywords dual antibacterial action, zwitterionic hydrogel, non-fouling, antimicrobial
目 次
1 绪论 . 1