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Synthesis of primary amine- and glyco-based methacrylamide polymers via the reversible addition-fragmentation chain transfer process.

机译:通过可逆的加成-断裂链转移过程合成伯胺和基于糖的甲基丙烯酰胺聚合物。

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摘要

Herein, a novel direct method is reported for the synthesis of primary aminoalkyl methacrylamides that requires mild reagents and no protecting group chemistry. The reversible addition-fragmentation chain transfer polymerization (RAFT) of the aminoalkyl methacrylamide revealed to be highly efficient with 4-cyanopentanoic acid dithiobenzoate (CTP) as chain transfer agent and 4,4'-azobis(4-cyanovaleric acid) (ACVA) as initiator. Cationic amino-based homopolymers of reasonably narrow polydispersity index (Mw/M n1.30) and predetermined molecular weights were obtained without recourse to any protecting group chemistry. A range of block and random copolymers were also synthesized via the RAFT process. The homopolymers and copolymers were characterized by aqueous conventional and triple detection gel permeation chromatography (GPC) systems. Furthermore, stabilities of the primary amine-based methacrylamide monomers and polymers were studied and revealed to be highly stable with the primary amino group both in the protonated and deprotonated form.;With high activity and stability, aminoalkyl methacrylamides can be used as powerful precursors to synthesize more exciting novel monomers. As an example of the derivatives of highly stable aminoalkyl methacrylamids, novel gluconamidoalkyl methacrylamides were directly synthesized by reacting D-gluconolactone with aminoalkyl methacrylamides. The glycomonomers were then successfully polymerized via the RAFT using CTP as chain transfer agent and ACVA as the initiator in aqueous media. Well-defined polymers were obtained as revealed by gel permeation chromatography. Multi-functional diblock copolymers, especially primary amine-based cationic glycopolymers were then synthesized by the macro-CTA approach.
机译:本文中,报道了新颖的直接方法用于合成伯氨基烷基甲基丙烯酰胺,该方法需要温和的试剂并且不需要保护基化学。氨基烷基甲基丙烯酰胺的可逆加成-断裂链转移聚合(RAFT)显示出以4-氰基戊酸二硫代苯甲酸酯(CTP)作为链转移剂和4,4'-偶氮双(4-氰基戊酸)(ACVA)作为高效化合物启动器。在不依赖任何保护基化学的情况下,获得了具有相当窄的多分散指数(Mw / M n <1.30)和预定分子量的阳离子氨基基均聚物。还通过RAFT方法合成了一系列嵌段和无规共聚物。均聚物和共聚物通过水性常规和三重检测凝胶渗透色谱(GPC)系统进行表征。此外,对伯胺基甲基丙烯酰胺单体和聚合物的稳定性进行了研究,结果表明它们与伯氨基的质子化和去质子化形式均具有很高的稳定性。合成更多令人兴奋的新型单体。作为高度稳定的氨基烷基甲基丙烯酰胺衍生物的实例,通过使D-葡糖酸内酯与氨基烷基甲基丙烯酰胺反应直接合成了新颖的葡糖酰胺基烷基甲基丙烯酰胺。然后,使用CTP作为链转移剂和ACVA作为引发剂,通过RAFT在水介质中成功地使糖单体聚合。如凝胶渗透色谱法所示,获得了定义明确的聚合物。然后通过宏观CTA方法合成多功能二嵌段共聚物,特别是伯胺基阳离子糖聚合物。

著录项

  • 作者

    Deng, Zhicheng.;

  • 作者单位

    Laurentian University (Canada).;

  • 授予单位 Laurentian University (Canada).;
  • 学科 Chemistry Organic.;Chemistry Polymer.
  • 学位 M.Sc.
  • 年度 2008
  • 页码 116 p.
  • 总页数 116
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;高分子化学(高聚物);
  • 关键词

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