Design and Construction of Furan and Thiophene‐Based Salicyladazine Bisbenzoxazine Resins with High Thermal Stability and Tunable Surface Properties

IF 2.5 4区化学 Q3 POLYMER SCIENCE

Macromolecular Chemistry and Physics Pub Date : 2024-05-31 DOI:10.1002/macp.202400091

Yang‐Chin Kao, Mohamed Gamal Mohamed, Chia‐Husan Chiang, Shiao‐Wei Kuo

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引用次数: 0

Abstract

We synthesized two disubstituted bisbenzoxazine monomers using furan (Fa) and thiophene (Th) derivatives: bis((3‐(furan‐2‐ylmethyl)‐7‐ol‐3,4‐dihydro‐2H‐benzo[e][1,3] oxazin‐6‐yl)methylene)hydrazine (BAZ‐Fa‐BZ) and bis((3‐(thiophen‐2‐ylmethyl)‐7‐ol‐3,4‐dihydro‐2H‐benzo[e][1,3] oxazin‐6‐yl)methylene)hydrazine (BAZ‐Th‐BZ). These monomers were synthesized via Mannich condensation of salicylaldazine (BAZ‐4OH) and paraformaldehyde (CH2O) with furfurylamine (Fa‐NH2) and thiophene‐2‐methenamine (Th‐NH2), respectively. The chemical structures of BAZ‐Fa‐BZ and BAZ‐Th‐BZ were affirmed using FT‐IR and NMR; respectively. A thorough investigation of the thermal polymerization process of BAZ‐Fa‐BZ and BAZ‐Th‐BZ was conducted using DSC, TGA, and in situ FT‐IR spectra (ranging from 25 to 250 °C). Poly(BAZ‐Fa‐BZ) exhibited superior thermal properties with a thermal decomposition temperature (Td10) of 402 °C and a char yield of 58 wt.% after thermal treatment at 250 °C, along with a lower surface free energy of 28.9 mJ m−2 compared to poly(BAZ‐Th‐BZ) (Td10 = 359 °C, char yield = 48 wt.%, and surface free energy = 34.1 mJ m−2). Additionally, poly(BAZ‐Th‐BZ/BAZ‐Fa‐BZ) blend with a ratio of 1/3 after thermal curing at 250 °C demonstrated the highest Td10 of 395 °C and a char yield of 60 wt.%. Photoluminescence (PL) measurements conducted in the solid state revealed that BAZ‐Th‐BZ, BAZ‐Fa‐BZ, and their blends emit green light when excited at a wavelength of 365 nm.This article is protected by copyright. All rights reserved

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设计和构建具有高热稳定性和可调表面特性的呋喃和噻吩基水杨醛双苯并恶嗪树脂

我们利用呋喃（Fa）和噻吩（Th）衍生物合成了两种二取代双苯并恶嗪单体：双((3-(呋喃-2-基甲基)-7-醇-3,4-二氢-2H-苯并[e][1,3] 恶嗪-6-基)亚甲基)肼 (BAZ-Fa-BZ) 和双((3-(噻吩-2-基甲基)-7-醇-3,4-二氢-2H-苯并[e][1,3] 恶嗪-6-基)亚甲基)肼 (BAZ-Th-BZ)。这些单体分别是通过水杨醛嗪（BAZ-4OH）和多聚甲醛（CH2O）与糠胺（Fa-NH2）和噻吩-2-甲胺（Th-NH2）的曼尼希缩合反应合成的。利用傅立叶变换红外光谱和核磁共振分别确定了 BAZ-Fa-BZ 和 BAZ-Th-BZ 的化学结构。利用 DSC、TGA 和原位傅立叶变换红外光谱（25 至 250 °C）对 BAZ-Fa-BZ 和 BAZ-Th-BZ 的热聚合过程进行了深入研究。与聚(BAZ-Th-BZ)（Td10 = 359 °C，焦炭产率 = 48 wt.%，表面自由能 = 34.1 mJ m-2）相比，聚(BAZ-Fa-BZ)的热分解温度（Td10）为 402 °C，250 °C热处理后的焦炭产率为 58 wt.%，表面自由能更低，为 28.9 mJ m-2。此外，在 250 °C 热固化后，比例为 1/3 的聚(BAZ-Th-BZ/BAZ-Fa-BZ)共混物的 Td10 最高，为 395 °C，产炭量为 60 wt.%。在固态下进行的光致发光（PL）测量显示，BAZ-Th-BZ、BAZ-Fa-BZ 及其混合物在波长为 365 nm 的激发下会发出绿光。本文受版权保护。

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来源期刊

Macromolecular Chemistry and Physics 化学-高分子科学

CiteScore

4.30

自引率

4.00%

发文量

278

审稿时长

1.4 months

期刊介绍： Macromolecular Chemistry and Physics publishes in all areas of polymer science - from chemistry, physical chemistry, and physics of polymers to polymers in materials science. Beside an attractive mixture of high-quality Full Papers, Trends, and Highlights, the journal offers a unique article type dedicated to young scientists – Talent.