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: 9135298
• 负责人: Christopher N Bowman
• 金额: $ 45.9万
• 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/9135298
• 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; Enzymes; Esters; Failure; Fatigue; Filler; Formulation; Fracture; Gel; Glass; Goals; Grant; Growth; Health; Hydrogen Bonding; Kinetics; Lead; Life; Mechanics; Methacrylates; Names; Nature; Oxygen; Performance; Phase; Plant Resins; Polymers; Property; Reaction; 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; restoration; restorative composite; restorative dentistry; restorative material; triethylene glycol dimethacrylate; uptake

DESCRIPTION (provided by applicant): 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-covalen 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.

描述（由申请人提供）：每年进行的超过一亿个牙科修复体中，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，但这些复合材料却遭受了限制其适用性和效用的重大问题。基于将近50年前开发和实施的树脂化学，这些材料的问题包括与可提取的，无反应的单体相关的问题，治愈后，单体的降解和复合材料的降解以及聚合收缩和收缩应激，诱发的压力，通过韧性和其他机械性材料和其他机械性材料和其他机械性能，并进行了较长的时间范围，并进行了较长的时间范围。由于少于8年的使用寿命，这些问题的结果通常是复合修复体的过早失败，这是由于次要龋齿或散装内或界面内的机械故障而导致的。我们建议基于现在经典的“点击”反应开发和评估复合恢复系统，即铜催化叠氮化物（CUAAC）反应。它的特征包括在没有副反应的情况下实现高转化率，在环境中稳健且很容易执行，并形成不容易被酸，水或酶降解的产物。此外，该反应的乘积是一种三唑环结构，能够具有二级分子相互作用（即非可瓦键形成），从而增强了交联聚合物材料的韧性，玻璃过渡和模量。因此，这项研究将通过（i）通过（i）为这些复合材料的树脂部分开发一种全新的方法来解决甲基丙烯酸酯复合系统的关键缺点，以使CuAAC反应以一种方式，以一种将导致实现近量化功能群体转化的方式，从而限制了可提取的单体，从而取得了限制降低水解质量的潜在，从而取得了降低的降级，从而取得了降低的质量质量，从而取得了降低的降低质量。收缩和压力； （ii）将这种新颖的基于CUAAC的树脂相与适当功能化的填充剂相结合，以实现所需的机械性能，改善断裂韧性，扩大这些修复的寿命，并实现复合材料的增强尺寸稳定性； （iii）分析这些树脂和复合材料的粘附，降解，提取和其他长期性能指标。照片引起的CuAAC聚合系统非常适合下一代牙科修复，我们的目标是开发与当前的牙科实践和粘合剂兼容的复合系统，但这些修复剂的使用寿命至少增加了两倍。