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Controlled RAFT synthesis of side-chain oleic acid containing polymers and their post-polymerization functionalization

机译：含侧链油酸的聚合物的受控RAFT合成及其聚合后官能化

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摘要

This study provides new insights into the design and controlled synthesis of side-chain unsaturated fatty acid containing polymers, with specific attention to facile post-polymerization modification reactions. The methacrylate derivative of oleic acid, 2-(methacryloyloxy)ethyl oleate (MAEO), has been synthesized and polymerized by the reversible addition-fragmentation chain transfer (RAFT) process to obtain poly(2( methacryloyloxy) ethyl oleate) (PMAEO) with controlled molecular weight, narrow molecular weight distribution (D) and known chain ends. The PMAEO is capable of subsequent chain extension to form well-defined block copolymers via the RAFT technique. Double bonds in the oleate side-chains in PMAEO are further reacted with various organic thiol compounds via thiol-ene based thia-Michael addition reactions in the presence of 2,2'-azobisisobutyronitrile (AIBN) as radical source at 60 degrees C in tetrahydrofuran (THF) solvent. H-1 NMR spectroscopy indicated quantitative conversion of double bonds with ethanethiol, butanethiol, dodecanethiol and 3-mercaptopropanoic acid, whereas 2-mercaptoethanol gave similar to 90% thioether product. The side-chain double bonds of PMAEO were quantitatively epoxidized using meta-chloroperbenzoic acid (mCPBA) at room temperature in dichloromethane, which was further cross-linked by 1,3-diaminopropane. Therefore, side-chain oleate pendants are ideal for various post-polymerization modifications to prepare renewable resource derived controlled macromolecular architectures with potential practical applications in fields such as paints, adhesives, electrical insulators, thermoplastics, etc.
机译：这项研究为含侧链不饱和脂肪酸的聚合物的设计和受控合成提供了新的见识，特别关注了容易的聚合后修饰反应。已通过可逆加成-断裂链转移（RAFT）工艺合成并聚合了油酸的甲基丙烯酸酯2-（甲基丙烯酰氧基）乙基油酸酯（MAEO），并使其与聚（2（甲基丙烯酰氧基）乙基油酸酯）（PMAEO）聚合。控制分子量，窄分子量分布（D）和已知链端。 PMAEO能够随后通过RAFT技术扩链，形成定义明确的嵌段共聚物。在2,2'-偶氮二异丁腈（AIBN）作为自由基源在60°C的四氢呋喃中存在下，PMAEO中油酸酯侧链中的双键通过基于硫醇-烯的thia-Michael加成反应与各种有机硫醇化合物进一步反应（THF）溶剂。 H-1 NMR光谱表明双键与乙硫醇，丁硫醇，十二烷硫醇和3-巯基丙酸的定量转化，而2-巯基乙醇得到的硫醚产物接近90％。在室温下，使用间氯过苯甲酸（mCPBA）在二氯甲烷中将PMEAO的侧链双键定量环氧化，然后再通过1,3-二氨基丙烷进行交联。因此，侧链油酸酯侧基非常适合进行各种聚合后修饰，以制备可再生资源衍生的受控大分子结构，在涂料，粘合剂，电绝缘体，热塑性塑料等领域具有潜在的实际应用。

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