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Opening New Gates for the Modification of PVC or Other PVC Derivatives: Synthetic Strategies for the Covalent Binding of Molecules to PVC

机译:为修饰PVC或其他PVC衍生物打开新的大门:分子与PVC共价结合的合成策略

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摘要

Several synthetic strategies based on the use of substituted aromatic and hetero-aromatic thiols for the covalent binding of modifier compounds to PVC are described. A variety of aliphatic alcohols and amines are linked to the aromatic or heteroaromatic rings via highly active functionalities as the isocyanate, acidchloride, or chlorosulfonyl group, and the three chlorine atoms of trichlorotriazine. The first three pathways lead to protected aromatic disulfides obtaining the substituted aromatic thiols by reduction as a final step of an unprecedented synthetic route. The second approach, in a novel, extremely efficient, and scalable process, uses the particular selectivity of trichlorotriazine to connect aliphatic amines, alcohols, and thiols to the ring and creates the thiol via nucleophilic substitution of a heteroaromatic halogen by thiourea and subsequent hydrolysis. Most of the modifier compounds were linked to the polymer chains with high degrees of anchorage. The presented approaches are highly versatile as different activations of aromatic and heteroaromatic rings are used. Therefore, many types of tailored functional nucleophiles may be anchored to PVC providing non-migrating materials with a broad range of applications and properties.
机译:描述了基于使用取代的芳族和杂芳族硫醇使改性剂化合物与PVC共价结合的几种合成策略。各种脂族醇和胺通过高活性官能团(如异氰酸酯,酰氯或氯磺酰基)和三氯三嗪的三个氯原子与芳族或杂芳族环相连。前三个途径导致受保护的芳族二硫化物通过还原获得了取代的芳族硫醇,这是前所未有的合成路线的最后一步。第二种方法是在新颖,高效且可扩展的方法中,使用三氯三嗪的特定选择性将脂族胺,醇和硫醇连接到环上,并通过硫脲将杂芳族卤素进行亲核取代并随后水解来生成硫醇。大多数改性剂化合物都以高度锚定度连接到聚合物链上。由于使用了芳族和杂芳族环的不同活化,因此所提出的方法是高度通用的。因此,许多类型的定制功能亲核试剂可以固定在PVC上,从而提供具有广泛应用和特性的非迁移材料。

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