Synthesis, homopolymerization and properties of p-aminopyridine methacrylate

IF 0.2 Q4 CHEMISTRY, MULTIDISCIPLINARY
V. E. Vakhabova, K. G. Guliev
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引用次数: 0

Abstract

For the first time, p-aminopyridine methacrylate was synthesized by a reaction between p-aminopyridine and methacryloyl chloride. IR and NMR spectroscopy сonfirmed the obtained compound structure. Radical homopolymerization of synthesized p-aminopyridine methacrylate was carried out either in bulk or in benzene solution (initiator – AIBN). The study of radical polymerization regularities of p-aminopyridine methacrylate discovered no side reactions and induction period of the reported process under the created conditions with a maximum yield of 92%. It was found that p-aminopyridine methacrylate is a more reactive monomer in radical polymerization as compared to methyl methacrylate. The structure of the obtained monomer and polymer was investigated by IR and NMR spectroscopy. Based on these data, the polymerization proceeds by a double bond, with substituents in the side macro chain remaining unreacted. The study of the synthesized monomer polymerization in the bulk indicated the presence of the gel effect. The autoacceleration begins at ~25% monomer conversion during the polymerization process, which agrees with the literature data. It was discovered that the polymerization of p-aminopyridine methacrylate proceeds at a rate higher than that of methyl methacrylate. This observation is likely to be connected with the substituent contribution to the electronic state of the entire monomer molecule. Hence, the electron density of the vinyl group changes and the growing radical becomes stabilized with the substituent –M-effect. The polymer synthesized possesses high antimicrobial properties.
对氨基吡啶甲基丙烯酸酯的合成、均聚及性能研究
以对氨基吡啶和甲基丙烯酰氯为原料,首次合成了对氨基吡啶甲基丙烯酸酯。红外光谱和核磁共振光谱证实了所得化合物的结构。合成的对氨基吡啶甲基丙烯酸酯在散装或苯溶液(引发剂- AIBN)中进行自由基均聚。对甲基丙烯酸对氨基吡啶自由基聚合规律的研究发现,在所创造的条件下,所报道的工艺无副反应和诱导期,收率最高可达92%。发现甲基丙烯酸对氨基吡啶在自由基聚合中是一种比甲基丙烯酸甲酯更活跃的单体。用红外光谱和核磁共振光谱对所得单体和聚合物的结构进行了表征。根据这些数据,聚合通过双键进行,侧宏链上的取代基保持未反应。对合成的单体聚合体进行了研究,表明存在凝胶效应。聚合过程中单体转化率在~25%时开始出现自加速现象,与文献数据一致。发现对氨基吡啶甲基丙烯酸酯的聚合速度高于甲基丙烯酸甲酯的聚合速度。这一观察结果很可能与取代基对整个单体分子电子态的贡献有关。因此,乙烯基的电子密度发生了变化,生长中的自由基在取代基- m效应下变得稳定。所合成的聚合物具有较高的抗菌性能。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
自引率
50.00%
发文量
63
审稿时长
12 weeks
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