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Facile Mechanochemical Preparation of Polyamide-derivatives via Solid-state Benzoxazine-isocyanide Chemistry
Chinese Journal of Polymer Science ( IF 4.3 ) Pub Date : 2020-10-14 , DOI: 10.1007/s10118-021-2510-6
Xu Sun , Wei Shi , Xin-Yu Zhou , Sheng Ding

With the exploration of novel sustainable protocol for functional polyamides’ (PAs) construction as the starting point, herein, the small molecular model compound (M1-ssBIC) was prepared firstly by manual grinding of monofunctional benzoxazine (1a) and isocyanide (1b) via solid-state benzoxazine-isocyanide chemistry (ssBIC) to evaluate the feasibility of ssBIC. Linear PAs (P1-series polymers) were subsequently synthesized from biunctional benzoxazine (2a) and isocyanide (2b), and the influence of the loading of catalyst (octylphosphonic acid) (OPA) on the polymerization was investigated. Afterwards, two kinds of cross-linked PAs were successfully constructed via ssBIC by using trifunctional benzoxazine (3a) and cross-linked polybenzoxazine (4a) as reaction substrates, respectively, thus verifying the adaptability of ssBIC. Structural characterization indicates that amide, phenolic hydroxyl and tertiary amine substructures, with metal-complexing capability, have been successfully integrated into the obtained PAs. A type of representative PA/silver composite (P3-AgNPs) was prepared subsequently via in situ reduction treatment, and its application as recyclable reduction catalyst for organic pollutant p-nitrophenol (4-NP) was preliminarily investigated here to provide the example for possible downstream application of ssBIC. We think that this current work could provide a new pathway for the construction of functional PAs through facile and sustainable ssBIC protocol.



中文翻译:

固态苯并恶嗪-异氰化物化学法快速简便地机械制备聚酰胺衍生物

以探索功能性聚酰胺(PAs)的新型可持续发展协议为出发点,本文首先通过手动研磨单功能苯并恶嗪(1a)和异氰酸酯(1b)制备小分子模型化合物(M1-ssBIC)固态苯并恶嗪-异氰化物化学(ssBIC)来评估ssBIC的可行性。随后由两官能苯并恶嗪(2a)和异氰酸酯(2b)合成线性PA(P1系列聚合物),并研究了催化剂(辛基膦酸)(OPA)的负载量对聚合的影响。之后,成功地通过两种方法构建了两种交联的PAssBIC分别使用三官能苯并恶嗪(3a)和交联聚苯并恶嗪(4a)作为反应底物,从而验证了ssBIC的适应性。结构表征表明,具有金属络合能力的酰胺,酚羟基和叔胺亚结构已成功整合到获得的PA中。随后通过原位还原处理制备了一种代表性的PA /银复合材料(P3-AgNPs),并在此初步研究了其作为有机污染物对硝基苯酚(4-NP)的可回收还原催化剂的应用,以提供可能的示例。 ssBIC的下游应用。我们认为,当前的工作可以通过便捷且可持续的ssBIC协议为功能性PA的构建提供一条新途径。

更新日期:2020-10-17
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