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High Molecular Weight Unsaturated Copolyesters Derived from Fully Biobased trans-β-Hydromuconic Acid and Fumaric Acid with 1,4-Butanediol: Synthesis and Thermomechanical Properties
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2019-03-07 00:00:00 , DOI: 10.1021/acssuschemeng.8b06334 Yang Yu 1 , Haocheng Xiong 1 , Jingyu Xiao 1 , Xuedan Qian 1 , Xuefei Leng 1 , Zhiyong Wei 1 , Yang Li 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2019-03-07 00:00:00 , DOI: 10.1021/acssuschemeng.8b06334 Yang Yu 1 , Haocheng Xiong 1 , Jingyu Xiao 1 , Xuedan Qian 1 , Xuefei Leng 1 , Zhiyong Wei 1 , Yang Li 1
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This work describes the synthesis, structure, and physical and thermomechanical properties of fully biobased unsaturated copolyesters via melt-polycondensation of renewable monomers trans-β-hydromuconic acid and fumaric acid with 1,4-butanediol conducted by a two-step polymerization employing stannous octoate as a catalyst and 4-methoxyphenol as a radical inhibitor. The polymerization conditions, including catalyst amount, second-stage reaction temperature, and time, were optimized to prepare high molecular mass unsaturated copolyesters without isomerization and saturation reaction in the unsaturated double bonds. Consequently, a series of poly(butylene hydromuconoate-co-butylene fumarate) (PBHBF) samples with weight-average molecular weight over 80 kg/mol were obtained. The chemical structures identified by 1H and 13C NMR indicated that the notorious side reactions of isomerization and saturation of C═C bonds in unsaturated polyesters were eliminated in the obtained PBHBF copolyesters. From the physical property analyses by wide-angle X-ray diffraction (WAXD), polarized optical microscopy (POM), and differential scanning calorimetry (DSC), semicrystalline nature was evidenced for all the samples; furthermore, isodimorphic behavior was observed in this copolyester system. The crystallinity degree and thermal properties including glass transition, melting, and crystallization temperatures could be effectively adjusted by controlling the comonomer composition. The resulting copolyesters exhibited excellent tensile properties, which were comparable or even superior to those of polyethylene and most well-known saturated aliphatic polyesters. Overall, these biobased unsaturated polyesters with superior thermomechanical properties and potential biodegradation appear to be the promising materials for practical applications.
中文翻译：
完全生物基反式-β-羟基果糖酸和富马酸与1,4-丁二醇衍生的高分子量不饱和共聚酯：合成和热力学性质
这项工作描述了全生物基不饱和共聚酯的合成，结构以及物理和热机械性质，这是通过可再生单体反式β-氢粘康酸和富马酸与辛酸亚锡的两步聚合反应，与1，4-丁二醇进行熔融缩聚而得到的。作为催化剂和4-甲氧基苯酚作为自由基抑制剂。优化聚合条件，包括催化剂量，第二阶段反应温度和时间，以制备高分子量的不饱和共聚酯，而在不饱和双键中不发生异构化和饱和反应。因此，一系列的聚（氢丁酸丁二醇酯）共聚物获得重均分子量超过80 kg / mol的富马酸丁二酯（PBHBF）样品。由1 H和13标识的化学结构1 H NMR表明，在所得的PBHBF共聚酯中，消除了不饱和聚酯中异构化和C═C键饱和的臭名昭著的副反应。通过广角X射线衍射（WAXD），偏振光学显微镜（POM）和差示扫描量热法（DSC）进行的物理性质分析，证明了所有样品均具有半结晶性质。此外，在该共聚酯体系中观察到了同晶行为。通过控制共聚单体组成，可以有效地调节结晶度和热性能，包括玻璃化转变，熔融和结晶温度。所得共聚酯表现出优异的拉伸性能，其与聚乙烯和最熟知的饱和脂族聚酯的拉伸性能相当或什至更好。全面的，
更新日期：2019-03-07
中文翻译：
完全生物基反式-β-羟基果糖酸和富马酸与1,4-丁二醇衍生的高分子量不饱和共聚酯：合成和热力学性质
这项工作描述了全生物基不饱和共聚酯的合成，结构以及物理和热机械性质，这是通过可再生单体反式β-氢粘康酸和富马酸与辛酸亚锡的两步聚合反应，与1，4-丁二醇进行熔融缩聚而得到的。作为催化剂和4-甲氧基苯酚作为自由基抑制剂。优化聚合条件，包括催化剂量，第二阶段反应温度和时间，以制备高分子量的不饱和共聚酯，而在不饱和双键中不发生异构化和饱和反应。因此，一系列的聚（氢丁酸丁二醇酯）共聚物获得重均分子量超过80 kg / mol的富马酸丁二酯（PBHBF）样品。由1 H和13标识的化学结构1 H NMR表明，在所得的PBHBF共聚酯中，消除了不饱和聚酯中异构化和C═C键饱和的臭名昭著的副反应。通过广角X射线衍射（WAXD），偏振光学显微镜（POM）和差示扫描量热法（DSC）进行的物理性质分析，证明了所有样品均具有半结晶性质。此外，在该共聚酯体系中观察到了同晶行为。通过控制共聚单体组成，可以有效地调节结晶度和热性能，包括玻璃化转变，熔融和结晶温度。所得共聚酯表现出优异的拉伸性能，其与聚乙烯和最熟知的饱和脂族聚酯的拉伸性能相当或什至更好。全面的，
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