Acylthiourea oligomers as promising reducing agents for dimethacrylate-based two-component dental materials

IF 4.6 1区 医学 Q1 DENTISTRY, ORAL SURGERY & MEDICINE
Yohann Catel, Jörg Angermann, Benjamin Grob, Pascal Fässler, Iris Lamparth, Thomas Schnur
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引用次数: 0

Abstract

Objectives

Currently used thiourea-based two-component dental materials may release bitter compounds if they are not properly cured. To address this issue, the objective of this study was to evaluate the potential of acylthiourea oligomers as reducing agents for the development of self-cure composites.

Methods

Acylthiourea oligomers ATUO1–3 were synthesized via cotelomerization of the acylthiourea methacrylate ATU1 with butyl methacrylate. They were characterized by 1H NMR spectroscopy and size exclusion chromatography. Self-cure composites based on the redox initiator system cumene hydroperoxide/acylthiourea oligomer/copper(II) acetylacetonate were formulated. The flexural strength and modulus were measured using a three-point bending setup. The double bond conversions were determined using NIR spectroscopy. The working time of each self-cure composite was measured using an oscillating rheometer. Leaching experiments using light-cure composites were performed in DMSO-d6.

Results

Acylthiourea oligomers ATUO1–3 were successfully synthesized in good yields. Both the oligomer molecular weight and the amount of thiourea groups were varied. Self-cure composites containing ATUO1 or ATUO2 as reducing agents exhibited excellent mechanical properties and high double-bond conversions. The amounts of reducing agent, cumene hydroperoxide and copper(II) acetylacetonate were shown to have a significant impact on the working time. Moreover, a correlation between flexural modulus and the amount of metal salt was clearly established. Self-cure composites containing the oligomer ATUO1 exhibited a longer working time than materials containing ATU1 or acetylthiourea. Contrary to acetylthiourea, ATUO1 was not able to leach out of light-cured composites.

Significance

Acylthiourea oligomers are promising reducing agents for the formulation of two-component dental materials that do not induce a bitter taste in mouth.

酰基硫脲低聚物作为二甲基丙烯酸酯基双组分牙科材料的还原剂
目的目前使用的硫脲基双组分牙科材料如果处理不当,可能会释放出苦味化合物。为了解决这一问题,本研究的目的是评估酰基硫脲低聚物作为自固化复合材料的还原剂的潜力。方法将甲基丙烯酸酰基硫脲ATU1与甲基丙烯酸丁酯共端粒化,合成巯基硫脲低聚物atu01 - 3。采用核磁共振氢谱和阻垢色谱对其进行了表征。制备了以过氧化氢异丙烯/酰基硫脲低聚物/乙酰丙酮铜为引发剂的自固化复合材料。弯曲强度和模量测量使用三点弯曲设置。双键转化用近红外光谱测定。用振荡流变仪测量了每种自固化复合材料的工作时间。在DMSO-d6中进行了光固化复合材料的浸出实验。结果成功合成了硫脲低聚物atu01 - 3。低聚物的分子量和硫脲基团的数量都发生了变化。以ATUO1或ATUO2为还原剂的自固化复合材料具有优异的力学性能和较高的双键转化率。还原剂、过氧化氢异丙苯和乙酰丙酮铜的用量对反应时间有显著影响。此外,弯曲模量与金属盐的量之间的相关性得到了明确的建立。含有低聚物ATU1的自固化复合材料比含有ATU1或乙酰硫脲的材料工作时间更长。与乙酰硫脲相反,ATUO1不能从光固化复合材料中浸出。意义酰基硫脲低聚物是制备双组份牙科材料的还原剂,在口腔中不会产生苦味。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Dental Materials
Dental Materials 工程技术-材料科学:生物材料
CiteScore
9.80
自引率
10.00%
发文量
290
审稿时长
67 days
期刊介绍: Dental Materials publishes original research, review articles, and short communications. Academy of Dental Materials members click here to register for free access to Dental Materials online. The principal aim of Dental Materials is to promote rapid communication of scientific information between academia, industry, and the dental practitioner. Original Manuscripts on clinical and laboratory research of basic and applied character which focus on the properties or performance of dental materials or the reaction of host tissues to materials are given priority publication. Other acceptable topics include application technology in clinical dentistry and dental laboratory technology. Comprehensive reviews and editorial commentaries on pertinent subjects will be considered.
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