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Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

ABSTRACT: Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were obtained.

SUBMITTER: Sinha J

PROVIDER: S-EPMC5875713 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

Sinha Jasmine J Podgórski Maciej M Huang Sijia S Bowman Christopher N CN

Chemical communications (Cambridge, England) 20180307 24

Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were obtained. ...[more]

PMID: 29512665

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Project description:Step-growth thiol-Michael photopolymerizable resins, constituting an alternative chemistry to the current methacrylate-based chain-growth polymerizations, were developed and evaluated for use as dental restorative materials. The beneficial features inherent to anion-mediated thiol-Michael polymerizations were explored, such as rapid photocuring, low stress generation, ester content tunability, and improved mechanical performance in a moist environment. An ester-free tetrafunctional thiol and a ultraviolet-sensitive photobase generator were implemented to facilitate thiol-Michael photopolymerization. Thiol-Michael resins of varied ester content were fabricated under suitable light activation. Polymerization kinetics and shrinkage stress were determined with Fourier-transform infrared spectroscopy coupled with tensometery measurements. Thermomechanical properties of new materials were evaluated by dynamic mechanical analysis and in 3-point bending stress-strain experiments. Photopolymerization kinetics, polymerization shrinkage stress, glass transition temperature, flexural modulus, flexural toughness, and water sorption/solubility were compared between different thiol-Michael systems and the BisGMA/TEGDMA control. Furthermore, the mechanical performance of 2 thiol-Michael composites and a control composite were compared before and after extensive conditioning in water. All photobase-catalyzed thiol-Michael polymerization matrices achieved >90% conversion with a dramatic reduction in shrinkage stress as compared with the unfilled dimethacrylate control. One prototype of ester-free thiol-Michael formulations had significantly better water uptake properties than the BisGMA/TEGDMA control system. Although exhibiting relatively lower Young's modulus and glass transition temperatures, highly uniform thiol-Michael materials achieved much higher toughness than the BisGMA/TEGDMA control. Moreover, low-ester thiol-Michael composite systems show stable mechanical performance even after extensive water treatment. Although further resin/curing methodology optimization is required, the photopolymerized thiol-Michael prototype resins can now be recognized as promising candidates for implementation in composite dental restorative materials.

Dataset Information

Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

Publications

Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

Similar Datasets

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