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

基本信息

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
项目类别：
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

项目摘要

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次牙齿修复中，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，但这些复合材料存在限制其适用性和实用性的重大问题。基于近 50 年前开发和实施的树脂化学，这些材料的问题包括与固化后存在可萃取的未反应单体、单体和复合材料的降解、聚合收缩和收缩引起的应力、聚合时间长相关的问题、树脂材料缺乏韧性和其他机械性能，聚合后样品吸收热量和水分。由于平均使用寿命不到 8 年，这些问题的结果往往是复合材料修复体过早失效，这是由于继发龋齿或本体内部或界面处的机械故障造成的。我们建议开发和评估基于现在经典的“点击”反应的复合修复系统，即铜催化叠氮化物-炔烃（CuAAC）反应。其特点包括实现高转化率、无副反应、稳定且易于在环境下进行，以及形成不易被酸、水或酶降解的产品。此外，反应产物是三唑环结构，其能够进行二级分子相互作用（即非共价键形成），从而增强交联聚合物材料的韧性、玻璃化转变和模量。因此，这项研究将通过以下方式解决甲基丙烯酸酯复合材料系统的关键缺点：(i) 开发一种全新的方法来处理这些复合材料的树脂部分，以实现近定量官能团转化的方式实施 CuAAC 反应，限制可萃取单体，消除水解和酶降解的可能性，通过二级分子相互作用提高机械性能，并显着减少收缩和应力； (ii) 将这种新型 CuAAC 基树脂相与适当功能化的填料相结合，以实现所需的机械性能，提高断裂韧性，延长这些修复体的使用寿命，并增强复合材料的尺寸稳定性； (iii) 分析这些树脂和复合材料的粘附、降解、萃取和其他长期性能指标。光诱导 CuAAC 聚合系统非常适合下一代牙科修复材料，我们的目标是开发一种与当前牙科实践和粘合剂兼容的复合系统，同时使牙齿修复材料的使用寿命至少延长两倍这些恢复剂。