Formaldehyde-Free Polybenzoxazines for High Performance Thermosets,Macromolecules

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Formaldehyde-Free Polybenzoxazines for High Performance Thermosets
Macromolecules ( IF 5.1 ) Pub Date : 2020-04-01 , DOI: 10.1021/acs.macromol.0c00192
Romain Tavernier ₁ , Lérys Granado ₁ , Gabriel Foyer ₂ , Ghislain David ₁ , Sylvain Caillol ₁

Affiliation

We report the synthesis and ring-opening polymerization of new formaldehyde-free benzoxazines. The polybenzoxazines obtained displayed high thermal stability and high char yields. Data from the literature combined with our analyses by differential scanning calorimetry and thermogravimetric analyses gave deeper understanding about the use of aromatic aldehydes instead of formaldehyde for the generation of polybenzoxazines. Using pyrolysis coupled with gas chromatography/mass spectrometry (Py-GC/MS) at different temperatures, we provided qualitative data to propose some polymerization and degradation mechanisms associated with these new structures. A dialdehyde was also used for the first time in order to obtain difunctional monomers, instead of using diamines or bisphenols. Interestingly, we demonstrated that formaldehyde, which is a CMR (carcinogenic, mutagenic, and/or reprotoxic) substance, could be avoided for the synthesis of polybenzoxazines without any loss of thermal performance. Finally, some interesting structure–properties relationships are herein discussed. In particular, the use of benzyl amines, rather than aromatic amines, was found to significantly increase the char yields.

中文翻译：

高性能热固性塑料的无甲醛聚苯并恶嗪

我们报告了新的无甲醛苯并恶嗪的合成和开环聚合。获得的聚苯并恶嗪显示出高的热稳定性和高的炭产率。来自文献的数据与我们通过差示扫描量热法和热重分析法进行的分析相结合，对使用芳族醛代替甲醛生成聚苯并恶嗪有了更深入的了解。使用热解结合气相色谱/质谱法（Py-GC / MS）在不同温度下，我们提供了定性数据，以提出一些与这些新结构相关的聚合和降解机理。为了获得双官能单体，还第一次使用二醛，而不是使用二胺或双酚。有趣的是，我们证明了甲醛，在合成聚苯并恶嗪时，可以避免使用CMR（致癌，诱变和/或生殖毒性）物质，而不会损失其热性能。最后，本文讨论了一些有趣的结构-属性关系。特别地，发现使用苄胺而不是芳族胺显着提高了焦炭收率。

更新日期：2020-04-24

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