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Highly Thermally Stable, Reversible and Flexible Main Chain-Type Benzoxazine Hybrid Incorporating Both Polydimethylsiloxane and Double-Decker-Shaped Polyhedral Silsesquioxane Units through Diels-Alder Reaction.

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We synthesized a new bifunctional furan derivative (PDMS-FBZ) through a sequence of hydrosilylation of nadic anhydride (ND) with polydimethylsiloxane (PDMS), reaction of the product with p-aminophenol to form PDMS-ND-OH, and… Click to show full abstract

We synthesized a new bifunctional furan derivative (PDMS-FBZ) through a sequence of hydrosilylation of nadic anhydride (ND) with polydimethylsiloxane (PDMS), reaction of the product with p-aminophenol to form PDMS-ND-OH, and its subsequent Mannich reaction with furfurylamine and CH2 O. We then prepared the main chain-type copolymer PDMS-DABZ-DDSQ through a Diels-Alder (DA) cycloaddition of PDMS-FBZ with the bismaleimide-functionalized double-decker silsesquioxane derivative DDSQ-BMI. Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy confirmed the structure of this PDMS-DABZ-DDSQ copolymer; differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and dynamic mechanical analysis (DMA) revealed it to have high flexibility and high thermal stability (Tg = 177°C; Td10 = 441°C; char yield = 60.1 wt%); contact angle measurements revealed a low surface free energy (18.18 mJ/m2 ) after thermal ring-opening polymerization, because the inorganic PDMS and DDSQ units were dispersed well, as revealed using scanning electron microscopy (SEM) and transmission electron microscopy (TEM). This PDMS-DABZ-DDSQ copolymer possessed reversible properties arising from the DA and retro-DA reactions, suggesting its possible application as a functional high-performance material. This article is protected by copyright. All rights reserved.

Keywords: reaction; main chain; chain type; diels alder; microscopy; pdms

Journal Title: Macromolecular rapid communications
Year Published: 2023

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