Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3 Street, 00-664 Warsaw, Poland.
Molecules. 2022 Jul 20;27(14):4627. doi: 10.3390/molecules27144627.
Glycerol polyesters have recently become objects of interest in tissue engineering. Barely known so far is poly(glycerol itaconate) (PGItc), a biocompatible, biodegradable polyester. Due to the presence of a C=C electron-acceptor moiety, it is possible to post-modify the product by Michael additions to change the properties of PGItc. Thus, using PGItc as one of the elements of cellular scaffold crosslinked in situ for bone tissue regeneration seems to be a very attractive yet unexplored solution. This work aims to optimize the synthesis of PGItc to obtain derivatives with a double bond in the side chain with the highest conversion rates. The experiments were performed with itaconic anhydride and glycerol using mathematical planning of experiments according to the Box-Behnken plan without solvent and catalyst. The input variables of the process were the ratio of the OH/COOH, temperature, and reaction time. The optimised output variables were: the degree of esterification (ED), the degree of esterification calculated from the analysis of H NMR spectra (ED), and the degree of itaconic anhydride conversion-calculation based on C NMR spectra (%X). In each of statistical models, the significance of the changed synthesis parameters was determined. Optimal conditions are when OH/COOH ratio is equal to 1.5, temperature is 140 °C and time of reaction is 5 h. The higher OH/COOH ratio, temperature and longer the experiment time, the higher the value of the degree of esterification and the degree of anhydride conversion.
聚甘油聚酯最近成为组织工程的研究对象。目前鲜为人知的是聚（甘油马来酸酯）（PGItc），一种具有生物相容性和可生物降解性的聚酯。由于存在 C=C 电子受体部分，可以通过迈克尔加成对产物进行后修饰，从而改变 PGItc 的性质。因此，将 PGItc 用作骨组织再生的细胞支架的交联元素之一，似乎是一种非常有吸引力但尚未探索的解决方案。本工作旨在优化 PGItc 的合成，以获得具有最高转化率的侧链双键的衍生物。实验采用马来酸酐和甘油，在无溶剂和催化剂的情况下，根据 Box-Behnken 计划进行数学实验设计。该过程的输入变量是 OH/COOH 的比例、温度和反应时间。优化的输出变量是酯化度（ED）、从 H NMR 光谱分析得出的酯化度（ED）和基于 C NMR 光谱计算的马来酸酐转化率（%X）。在每个统计模型中，都确定了改变合成参数的显著性。最佳条件是当 OH/COOH 比等于 1.5 时，温度为 140°C，反应时间为 5 小时。OH/COOH 比、温度越高，实验时间越长，酯化度和酸酐转化率的值越高。
