Cu-Catalyzed Azide-Alkyne Reactions for Novel Dental Composite Materials

铜催化叠氮化物-炔烃反应用于新型牙科复合材料

• 批准号: 8610736
• 负责人: Christopher N Bowman
• 金额: $ 49.94万
• 依托单位: UNIVERSITY OF COLORADO
• 依托单位国家: 美国
• 财政年份: 2013
• 资助国家: 美国
• 起止时间: 2013-09-01 至 2018-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/8610736
• 关键词: Achievement; Acids; Address; Adhesions; Adhesives; Alkynes; Azides; Behavior; Binding; Characteristics; Chemistry; Composite Resins; Copper; Coupling; Dental; Dental General Practice; Dental caries; Dentistry; Development; Drug Formulations; Enzymes; Esters; Failure; Fatigue; Filler; Fracture; Gel; Glass; Goals; Grant; Growth; Hydrogen Bonding; Kinetics; Lead; Life; Mechanics; Methacrylates; Metric; Names; Nature; Oxygen; Performance; Phase; Plant Resins; Polymers; Property; Reaction; Relative (related person); Research; Sampling; Services; Side; Stress; Structure; Surface; Swelling; System; Triazoles; Urethane; Viscosity; Visible Radiation; Water; Work; base; biomaterial compatibility; composite restoration; crosslink; cycloaddition; dental adhesive; functional group; improved; mechanical behavior; meetings; monomer; next generation; novel; novel strategies; photopolymerization; polymerization; polymerization shrinkage; premature; public health relevance; restoration; restorative composite; restorative dentistry; restorative material; triethylene glycol dimethacrylate; uptake

!"#!$%$&'()*+$(,*)#$&-'.)+/)$!%,0.1+20/+.03)&+*).%$&+!04501,%)+4$%)/,$&1+ + 1644$/'+ + More than 60% of the more than one hundred million dental restorations performed each year involve the use of photopolymerizable polymeric composites. Despite their ubiquitous presence in modern dentistry, these composites suffer from significant problems that limit their applicability and utility. Based on resin chemistry developed and implemented nearly 50 years ago, the problems with these materials include issues associated with the presence of extractable, unreacted monomer following cure, degradation of the monomers and composite, polymerization shrinkage and shrinkage induced stresses, the long timeframe for polymerization, lack of toughness and other mechanical behavior of the resin material, thermal and moisture uptake by the sample following polymerization. With less than an 8 year average service life, the result of these problems is often the premature failure of composite restorations, resulting either from secondary caries or from mechanical failure within the bulk or at the interface. We propose to develop and evaluate a composite restorative system based on the now-classic "click" reaction, that is the copper catalyzed azide-alkyne (CuAAC) reaction. Its characteristics include achieving high conversion without side reactions, being robust and readily performed at ambient, and forming a product that is not readily degradable by acids, water, or enzymes. Moreover, the product of the reaction is a triazole ring structure that is capable of secondary molecular interactions (i.e., non-covalent bond formation) that enhance toughness, glass transition, and modulus of the crosslinked polymer material. Thus, this research will address the critical shortcomings of methacrylate composite systems by (i) developing a completely new approach to the resin portion of these composites that implements the CuAAC reaction in a manner that will lead to achievement of near-quantitative functional group conversions, limit extractable monomers, eliminate the potential for hydrolytic and enzymatic degradation, improve the mechanical properties through secondary molecular interactions, and dramatically reduce shrinkage and stress; (ii) combining this novel CuAAC-based resin phase with appropriately functionalized fillers to achieve the desired mechanical performance, improve fracture toughness, extend the lifetime of these restorations, and achieve enhanced dimensional stability of the composite; and (iii) analyzing the adhesion, degradation, extraction, and other long-term performance metrics for these resins and composites. The photo-induced CuAAC polymerization system is ideally suited for the next generation of dental restoratives and our goal is the development of a composite system that is compatible with current dental practices and adhesives and yet yields at least a two fold increase in the service life of these restoratives. ! !

！”＃！$％$＆'（）*+$（，*）＃$＆ - '。）+/）$！％，0.1+20/+。03）＆+*）。％$＆+！04501，％）+4 $％）/，$＆1+ + 1644 $/'+ + 每年进行的超过一亿辆牙科修复体中，超过60％涉及 使用光聚合聚合物复合材料。尽管它们在现代牙科中无处不在，但这些 复合材料遭受了限制其适用性和效用的重大问题。基于树脂化学 这些材料的问题开发和实施了，这些材料的问题包括相关的问题 在治愈后存在可提取的，未反应的单体，单体降解和 复合，聚合收缩和收缩诱导的应力，是聚合的长时间， 树脂材料缺乏韧性和其他机械行为，热量和水分吸收 聚合后的样本。这些问题的平均服务寿命少于8年，这些问题的结果是 通常是由次要龋齿或来自 散装或界面内的机械故障。 我们建议基于现在经典的“点击”开发和评估复合修复系统 反应，即铜催化叠氮化物（CUAAC）反应。它的特征包括达到高 没有侧面反应的转换，在环境中稳健且容易执行，并形成一种产品 不容易被酸，水或酶降解。此外，反应的产物是三唑环 能够增强次级分子相互作用的结构（即非共价键形成） 交联聚合物材料的韧性，玻璃过渡和模量。因此，这项研究将解决 甲基丙烯酸酯复合系统的关键缺点（i）开发一种全新的方法 这些复合材料的树脂部分以导致的方式实现CuAAC反应 实现近量化功能组的转换，限制可提取的单体，消除 潜在的水解和酶促降解，通过二级提高机械性能 分子相互作用，并大大减少收缩和压力； （ii）结合这种新颖的基于CUAAC 树脂阶段具有适当功能化填充剂以实现所需的机械性能，改善 断裂韧性，延长这些修复的寿命，并实现增强的维度稳定性 合成的; （iii）分析粘附，降解，提取和其他长期性能指标 对于这些树脂和复合材料。照片诱导的CUAAC聚合系统非常适合 下一代牙科修复剂，我们的目标是开发一个复合系统 与当前的牙科实践和粘合剂兼容，但至少可以增加两倍的服务 这些恢复的生活。 呢 呢