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Phthalonitrile functionalized resoles – use of 2,3-dicyanohydroquinone as a versatile monomer for resins with very high thermal stability
Polymer Degradation and Stability ( IF 6.3 ) Pub Date : 2023-05-27 , DOI: 10.1016/j.polymdegradstab.2023.110420
Nathanaël Chaussoy , Damien Brandt , Jean-François Gérard

In the aerospace industry, composite materials based on high-performance fibers and polymer matrices are widely used. Indeed, they can display very important mechanical and thermal properties with a very large density-to-stiffness balance. Usually, thermal protection systems are made from composite materials containing a char precursor for the polymer matrix. Temperature-resistant organic polymers are still quite rare and generally require very restrictive manufacturing and use processes. Recently, phthalonitriles have gained interest due to their very good thermostability and high char yield. However, phthalonitrile resins are generally solid at room temperature and often have a narrow processing window. In this work, synthesis methods allowing access to phthalonitrile resins were developed from 2,3-dicyanohydroquinone. These methods propose to consider together phenolic chemistry (phenolic reactive positions and aldehyde) and self-crosslinkable phthalonitrile chemistry (hydroxyl-mediated from phenolic and nitriles). It was thus possible to synthesize liquid resins at room temperature, leading to polymeric networks with a very high thermostability (temperature at 5% mass loss > 450 °C and char yield ≈ 70 %).



中文翻译:

苯二甲腈功能化甲阶酚醛树脂——使用 2,3-二氰基氢醌作为具有非常高热稳定性的树脂的多功能单体

在航空航天工业中,以高性能纤维和聚合物基体为基础的复合材料得到广泛应用。事实上,它们可以显示非常重要的机械和热性能,具有非常大的密度与刚度平衡。通常,热保护系统由复合材料制成,其中包含用于聚合物基质的炭前体。耐温有机聚合物仍然非常稀有,通常需要非常严格的制造和使用过程。最近,邻苯二甲腈因其非常好的热稳定性和高炭产率而受到关注。然而,邻苯二甲腈树脂在室温下通常为固体,加工窗口通常较窄。在这项工作中,从 2,3-二氰基氢醌开发了允许获得邻苯二甲腈树脂的合成方法。这些方法建议同时考虑酚类化学(酚类反应位置和醛)和可自交联的苯二甲腈化学(由酚类和腈类介导的羟基)。因此可以在室温下合成液态树脂,从而形成具有非常高热稳定性的聚合物网络(5% 质量损失时的温度 > 450 °C,焦化率 ≈ 70 %)。

更新日期:2023-05-31
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