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A Facile Method to Synthesize Semicrystalline Poly(ester amide)s from 2,5-Furandicarboxylic Acid, 1,10-Decanediol, and Crystallizable Amido Diols
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-06-30 , DOI: 10.1021/acssuschemeng.0c02730 Marcel Kluge 1, 2 , Lazaros Papadopoulos 3 , Andreas Magaziotis 3 , Dimitrios Tzetzis 4 , Alexandra Zamboulis 3 , Dimitrios N. Bikiaris 3 , Tobias Robert 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-06-30 , DOI: 10.1021/acssuschemeng.0c02730 Marcel Kluge 1, 2 , Lazaros Papadopoulos 3 , Andreas Magaziotis 3 , Dimitrios Tzetzis 4 , Alexandra Zamboulis 3 , Dimitrios N. Bikiaris 3 , Tobias Robert 1
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The synthesis of polyamides and poly(ester amide)s derived from 2,5-furandicarboxylic acid frequently leads to amorphous polymeric materials. Formation of intramolecular hydrogen bonds between the oxygen heteroatom in the furan ring and hydrogens of the amide bonds reduces the intermolecular hydrogen bonds that are usually responsible for the high thermal and mechanical performance of these materials. To circumvent this problem, aliphatic–aromatic poly(ester amide)s were synthesized in this study from dimethyl 2,5-furandicarboxylate, 1,10-decanediol, and a preformed aliphatic diol containing two internal amide bonds (amido diol). Wide-angle X-ray diffraction and differential scanning calorimetry experiments revealed that polymers obtained were semicrystalline over the whole composition range and crystallized rapidly from the molten state, indicating that intramolecular H-bonding is effectively suppressed. Depending on the ratio of 1,10-decanediol and amido diol, the thermal properties could be adjusted over a wide temperature range. The polymers exhibit Tg and Tm in a range of −4 to 27 °C and 102 to 175 °C, respectively. Elastic modulus and hardness increased almost linearly with the amount of ester–amide moieties. The method presented herein allows for the successful synthesis of semicrystalline poly(ester amide)s from 2,5-furandicarboxylic acid without undesired intramolecular hydrogen bonds. This finding could set the stage for further bio-based poly(ester amide)s from 2,5-furandicarboxylic acid suitable for high-performance applications.
中文翻译：
一种由2,5-呋喃二甲酸，1,10-癸二醇和可结晶酰胺基二元醇合成半结晶聚（酯酰胺）的简便方法
由2，5-呋喃二甲酸衍生的聚酰胺和聚（酯酰胺）的合成经常导致无定形聚合材料。在呋喃环中的氧杂原子与酰胺键的氢之间形成分子内氢键会减少通常导致这些材料的高热和机械性能的分子间氢键。为了解决这个问题，在这项研究中，由2,5-呋喃二甲酸二甲酯，1,10-癸二醇和含有两个内部酰胺键的预制脂族二醇（酰胺二醇）合成了脂族-芳族聚（酯酰胺）。广角X射线衍射和差示扫描量热法实验表明，所获得的聚合物在整个组成范围内均为半结晶，并从熔融态迅速结晶，表明分子内的H键被有效地抑制。取决于1，10-癸二醇和酰氨基二醇的比例，可以在很宽的温度范围内调节热性能。聚合物表现出T g和T m分别在-4至27°C和102至175°C的范围内。弹性模量和硬度几乎随酯酰胺部分的数量线性增加。本文提出的方法允许由2，5-呋喃二甲酸成功合成半结晶聚（酯酰胺），而没有不希望的分子内氢键。这一发现可能为进一步开发适用于高性能应用的2,5-呋喃二甲酸生物基聚（酯酰胺）奠定基础。
更新日期：2020-07-27
中文翻译：
一种由2,5-呋喃二甲酸，1,10-癸二醇和可结晶酰胺基二元醇合成半结晶聚（酯酰胺）的简便方法
由2，5-呋喃二甲酸衍生的聚酰胺和聚（酯酰胺）的合成经常导致无定形聚合材料。在呋喃环中的氧杂原子与酰胺键的氢之间形成分子内氢键会减少通常导致这些材料的高热和机械性能的分子间氢键。为了解决这个问题，在这项研究中，由2,5-呋喃二甲酸二甲酯，1,10-癸二醇和含有两个内部酰胺键的预制脂族二醇（酰胺二醇）合成了脂族-芳族聚（酯酰胺）。广角X射线衍射和差示扫描量热法实验表明，所获得的聚合物在整个组成范围内均为半结晶，并从熔融态迅速结晶，表明分子内的H键被有效地抑制。取决于1，10-癸二醇和酰氨基二醇的比例，可以在很宽的温度范围内调节热性能。聚合物表现出T g和T m分别在-4至27°C和102至175°C的范围内。弹性模量和硬度几乎随酯酰胺部分的数量线性增加。本文提出的方法允许由2，5-呋喃二甲酸成功合成半结晶聚（酯酰胺），而没有不希望的分子内氢键。这一发现可能为进一步开发适用于高性能应用的2,5-呋喃二甲酸生物基聚（酯酰胺）奠定基础。
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