Sustainable bisphenols for thio-catechol adhesives: Fundamentals of scalable oxidation, polymerization, and light-switchable mechanisms of adhesion & debonding

用于硫代儿茶酚粘合剂的可持续双酚：可扩展氧化、聚合和光控粘合机制的基础知识

• 批准号: 536607484
• 负责人: Professor Dr. Hans Gerhard Börner
• 金额: --
• 依托单位: Arbeitsgruppe Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 资助国家: 德国
• 项目状态: 未结题
• 来源: https://gepris.dfg.de/gepris/projekt/536607484?language=en
• 关键词: Sustainable; bisphenols; thio; catechol; adhesives

The project focuses on the synthesis of nature-inspired TCC adhesives via thiol-quinone polyadditions, with an emphasis on the utilization of bioresources through the synergy of organic process development and material synthesis. The objectives of the planned investigations are twofold. On the side of organic method development (BUW, AK Kirsch), the focus will be on the investigation and establishment of a direct oxidation reaction of naturally occurring phenols to their corresponding quinones, while ensuring scalability and adherence to green principles. Since the standard reagent for this transformation, 2-iodoxybenzoic acid (IBX), is explosive in large quantities, the challenge is to develop batch and continuous catalytic processes for diphenol-bisquinone oxidation and to facilitate catalyst recyclability. On the side of material synthesis and polymer application (HUB, AK Börner), the study of sustainable bisquinones for the polymerization with multithiols is a key aspect, with the ultimate aim of enabling bio-based TCC-polymers suitable for adhesive applications. Using derivatives of the [2+2] photocyclization product of caffeic acid, TCC-polymer networks will be accessible and studied for their light-switchable cleavage and photoresponsive reorganization capability. These materials allow the exploration of highly demanded applications in the field of debonding and rebonding, but also the investigation of interesting concepts such as photostimulated healing of adhesion defects.

该项目的重点是通过硫酚-苯二酚多加成合成天然TCC胶粘剂，重点是通过有机工艺开发和材料合成的协同作用利用生物资源。计划中的调查目标有两个。在有机方法开发方面(BUW，AK Kirsch)，重点将是研究和建立自然产生的苯酚直接氧化反应为其相应的苯二酚，同时确保可伸缩性和遵守绿色原则。由于这种转化的标准试剂2-碘氧基苯甲酸(IBX)是爆炸性的，因此开发间歇和连续的催化过程来催化二苯酚-双苯二酚的氧化和促进催化剂的回收利用是一个挑战。在材料合成和聚合物应用方面(HUB，AK Börner)，研究用于多硫醇聚合的可持续双醌是一个关键方面，最终目的是使适合于粘合剂应用的生物基TCC聚合物成为可能。利用咖啡酸的[2+2]光环化产物的衍生物，TCC-聚合物网络将被访问并研究其光可切换的切割和光响应重组能力。这些材料不仅可以在脱粘和再粘合领域探索高要求的应用，而且还可以研究有趣的概念，如粘连缺陷的光刺激修复。