用于增粘单体配方的可聚合环糊精衍生物的合成。

IF 1.5 4区 工程技术
Rafael L Bowen, Clifton M Carey, Kathleen M Flynn, Charles M Guttman
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引用次数: 0

摘要

本文所报道的环糊精衍生物的合成得到了广泛的文献研究和三维分子建模得出的结构-性质关系的帮助。这些研究提出了一个假设:β-环糊精分子上的 21 个羟基中,有许多可以衍生化,形成一个密切相关的类似化合物家族,其中既含有可聚合基团,又含有亲水性可离子化配体(底物结合)基团,每个基团都通过水解稳定的醚键连接。乙烯基苄基醚可聚合基团很容易与甲基丙烯酸酯发生均聚和共聚。这对牙科应用非常有用,因为当代几乎所有的牙科树脂和复合材料都是以甲基丙烯酸酯单体为基础的。由于具有亲水性配体和残余羟基,这些环糊精衍生物应能穿透牙本质和珐琅质的水合层,与胶原蛋白和牙齿矿物质相互作用。分析表明,本文报告的合成方法所产生的各种反应产物应包括一系列可共聚的分子,这些分子上共含有约 30 种不同的乙烯基苄基和己酸酯基团组合,其中一些分子上的此类基团组合多达约 7 种。尽管假设得到了支持,而且使用这些可聚合环糊精衍生物有望显著改善与牙本质的粘合性,但我们还计划改进合成方法,以确保每个反应生成物分子至少含有一个可共聚的分子。长期目标是使密集交联的聚合物能够更牢固、更持久地附着在水合亲水基质上。将水解稳定的聚合物粘合到牙科组织或其他水合生物组织上的能力可带来广泛的益处。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations.

Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations.

Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations.

Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations.

The synthesis of the cyclodextrin derivatives reported herein was assisted by extensive literature research together with structure-property relationships derived from three-dimensional molecular modeling. These studies led to the hypothesis that many of the 21 hydroxyl groups on beta-cyclodextrin molecules could be derivatized to form a closely related family of analogous chemical compounds containing both polymerizable groups and hydrophilic ionizable ligand (substrate-binding) groups, each attached via hydrolytically-stable ether-linkages. The vinylbenzylether polymerizable groups should readily homopolymerize and also copolymerize with methacrylates. This could be highly useful for dental applications because substantially all contemporary dental resins and composites are based on methacrylate monomers. Due to hydrophilic ligands and residual hydroxyl groups, these cyclodextrin derivatives should penetrate hydrated layers of dentin and enamel to interact with collagen and tooth mineral. Analyses indicated that the diverse reaction products resulting from the method of synthesis reported herein should comprise a family of copolymerizable molecules that collectively contain about 30 different combinations of vinylbenzyl and hexanoate groups on the various molecules, with up to approximately seven of such groups combined on some of the molecules. Although the hypothesis was supported, and adhesive bonding to dentin is expected to be significantly improved by the use of these polymerizable cyclodextrin derivatives, other efforts are planned for improved synthetic methods to ensure that each of the reaction-product molecules will contain at least one copolymerizable moiety. The long-term objective is to enable stronger and more durable attachments of densely cross-linked polymers to hydrated hydrophilic substrates. Capabilities for bonding of hydrolytically stable polymers to dental and perhaps other hydrous biological tissues could provide widespread benefits.

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来源期刊
自引率
33.30%
发文量
10
期刊介绍: The Journal of Research of the National Institute of Standards and Technology is the flagship publication of the National Institute of Standards and Technology. It has been published under various titles and forms since 1904, with its roots as Scientific Papers issued as the Bulletin of the Bureau of Standards. In 1928, the Scientific Papers were combined with Technologic Papers, which reported results of investigations of material and methods of testing. This new publication was titled the Bureau of Standards Journal of Research. The Journal of Research of NIST reports NIST research and development in metrology and related fields of physical science, engineering, applied mathematics, statistics, biotechnology, information technology.
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