Hennig Kathleen, Vacun Gabriele, Thude Sibylle, Meyer Wolfdietrich
Department of Life Science and Bioprocesses, Fraunhofer Institute for Applied Polymer Research IAP, Geiselbergstr. 69, 14476 Potsdam-Golm, Germany.
Fraunhofer Institute for Interfacial Engineering and Biotechnology (IGB), Nobelstr. 12, 70569 Stuttgart, Germany.
Polymers (Basel). 2025 May 7;17(9):1285. doi: 10.3390/polym17091285.
This study explores the synthesis of photocurable non-isocyanate polyhydroxyethylurethanes (BPHUs) derived from renewable sources, designed for biomedical applications and the development towards advanced light curing processes. The following two pathways were developed: an aliphatic route using 1,4-butanediol-derived cyclic carbonates and an aromatic route with resorcinol-based carbonates. Ring-opening polymerization with dodecanediamine produced BPHU intermediates, which were methacrylated to form photoreactive derivatives (aliphatic MAs and aromatic MAs). Comprehensive characterization, including NMR, GPC, and FTIR, confirmed the successful synthesis. The UV curing of these methacrylated compounds yielded hydrogels with swelling properties. Aliphatic BPHUs achieved a gel content of 91.3% and a swelling of 1057%, demonstrating the flexibility and UV stability suitable for adaptable biomedical applications. Conversely, aromatic BPHUs displayed a gel content of 78.1% and a swelling of 3304%, indicating higher rigidity, which is advantageous for load-bearing uses. Cytotoxicity assessments adhering to the DIN EN ISO 10993-5 standard demonstrated non-cytotoxicity, with an >80% cell viability for both variants. This research underscores the potential of green chemistry in crafting biocompatible, versatile BPHUs, paving the way for eco-friendly materials in implantable medical devices.
本研究探索了源自可再生资源的光固化非异氰酸酯聚羟乙基聚氨酯（BPHU）的合成，其设计用于生物医学应用以及先进光固化工艺的开发。开发了以下两条途径：一条是使用1,4 - 丁二醇衍生的环状碳酸酯的脂肪族路线，另一条是使用间苯二酚基碳酸酯的芳香族路线。与十二烷二胺进行开环聚合反应生成BPHU中间体，将其甲基丙烯酸酯化以形成光反应性衍生物（脂肪族甲基丙烯酸酯和芳香族甲基丙烯酸酯）。包括核磁共振（NMR）、凝胶渗透色谱（GPC）和傅里叶变换红外光谱（FTIR）在内的全面表征证实了合成成功。这些甲基丙烯酸酯化化合物的紫外光固化产生了具有溶胀性能的水凝胶。脂肪族BPHU的凝胶含量达到91.3%，溶胀率为1057%，表明其具有适合适应性生物医学应用的柔韧性和紫外稳定性。相反，芳香族BPHU的凝胶含量为78.1%，溶胀率为3304%，表明其具有更高的刚性，这对于承重用途是有利的。按照DIN EN ISO 10993 - 5标准进行的细胞毒性评估表明两种变体均无细胞毒性，细胞活力均>80%。本研究强调了绿色化学在制造生物相容性、多功能BPHU方面的潜力，为可植入医疗设备中的环保材料铺平了道路。
