Tuning conditions for the amine-functionalization of carbonyls formed in biobased polyfurfuryl alcohol

IF 5.4 1区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY GIANT Pub Date : 2024-05-11 DOI:10.1016/j.giant.2024.100283

Pierre Delliere, Nathanael Guigo

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Abstract

Biobased furan resins (furfuryl alcohol based) are functionalized by taking advantage of a side-reaction occurring during its polymerization. The furan ring-opening reactions yields carbonyls which can be functionalized by reaction with primary amines. Light is shed on unexplored parameters impacting the properties of PFA/Amine systems. First, PFA/Amines were prepared using PFA resins at conversion degree between 0.3 and 0.95. Overall, high conversion degrees (0.9 and above) are best suited to produce rigid materials. In addition, a precipitation process may be used to reach high T_g biobased materials (145 °C). Finally, the impact of the amines’ basicity on the properties of PFA/Amines was investigated. The results highlighted that PFAs at conversion degrees above 0.9 are little affected by the basicity. However, the properties of PFA functionalized at lower conversion degrees are strongly affected by the bases, i.e. high brittleness. This can be circumvented by limiting the functionalization degree to 0.25 and below.

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生物基聚糠醇中形成的羰基胺功能化的调整条件。

生物基呋喃树脂（基于糠醇）是利用其聚合过程中发生的副反应进行功能化的。呋喃开环反应产生的羰基可通过与伯胺反应进行官能化。本研究揭示了影响 PFA/Amine 系统特性的未探索参数。首先，使用转化率在 0.3 至 0.95 之间的 PFA 树脂制备 PFA/胺。总体而言，高转化率（0.9 及以上）最适合生产刚性材料。此外，还可以使用沉淀工艺来达到生物基材料的高 Tg 值（145 °C）。最后，研究了胺的碱性对 PFA/Amines 性能的影响。结果表明，转化率高于 0.9 的 PFA 几乎不受碱性的影响。然而，转化度较低的官能化 PFA 的特性受碱的影响很大，即脆性较高。将官能化程度限制在 0.25 及以下可以避免这种情况。

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来源期刊

GIANT Multiple-

CiteScore

8.50

自引率

8.60%

发文量

审稿时长

42 days

期刊介绍： Giant is an interdisciplinary title focusing on fundamental and applied macromolecular science spanning all chemistry, physics, biology, and materials aspects of the field in the broadest sense. Key areas covered include macromolecular chemistry, supramolecular assembly, multiscale and multifunctional materials, organic-inorganic hybrid materials, biophysics, biomimetics and surface science. Core topics range from developments in synthesis, characterisation and assembly towards creating uniformly sized precision macromolecules with tailored properties, to the design and assembly of nanostructured materials in multiple dimensions, and further to the study of smart or living designer materials with tuneable multiscale properties.