Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

Reinelt, Sebastian; Tabatabai, Monir; Fischer, Urs; Moszner, Norbert; Utterodt, Andreas; Ritter, Helmut

doi:10.3762/bjoc.10.180

Cited by 19 publications

(19 citation statements)

References 36 publications

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“…For example to achieve better flexural strength ester free multifunctional thiols derived from an array of bisphenol structures were used. 37 Such materials showed also an improved performance in relation to PETMP/TTT after conditioning in water for 24 hours. Other reports described the use of ester-free thiol-ene materials as dental resins.…”

Section: Resultsmentioning

confidence: 98%

Ester-free thiol-X resins: new materials with enhanced mechanical behavior and solvent resistance

et al. 2015

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A series of thiol-Michael and radical thiol-ene network polymers were successfully prepared from ester-free as well as ester-containing monomer formulations. Polymerization reaction rates, dynamic mechanical analysis, and solvent resistance experiments were performed and compared between compositions with varied ester loading. The incorporation of ester-free alkyl thiol, vinyl sulfone and allylic monomers significantly improved the mechanical properties when compared with commercial, mercaptopropionate-based thiol-ene or thiol-Michael networks. For polymers with no hydrolytically degradable esters, glass transition temperatures (Tg's) as high as 100 °C were achieved. Importantly, solvent resistance tests demonstrated enhanced stability of ester-free formulations over PETMP-based polymers, especially in concentrated basic solutions. Kinetic analysis showed that glassy step-growth polymers are readily formed at ambient conditions with conversions reaching 80% and higher.

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Section: Resultsmentioning

confidence: 98%

Ester-free thiol-X resins: new materials with enhanced mechanical behavior and solvent resistance

et al. 2015

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“…The characterization of photocured thiol‐ene networks has mainly been focused on the structural parameters related to ene flexibility in the past . Although there are some reports describing the effect of different thiol monomers on the cured network, most of them deal with mercapto propionic acid derivatives such as PETMP, TMPMP, or pentaerythritol tetrakis (mercaptobutylate) . Basically, it is well documented that thermal and mechanical properties directly correspond to features inherent to the chemical structure of the ene and thiol monomer.…”

Section: Resultsmentioning

confidence: 99%

“…Although there is a vast number of studies describing the effect of different enes on the physicochemical properties of thiol‐ene polymers, there are only a few reports, which deal with alternative thiol compounds and their impact on the polymeric properties . Very recently, the group of Bowman and coworkers successfully demonstrated the beneficial behavior of ester‐free thiols based on the example of tetra(2‐mercaptoethyl)silane.…”

Section: Introductionmentioning

confidence: 99%

Silicon‐based mercaptans: High‐performance monomers for thiol‐ene photopolymerization

Roth

Oesterreicher

Mostegel

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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Ester‐free silane and siloxane‐based thiol monomers were successfully synthesized and evaluated for application in thiol‐ene resins. Polymerization reaction rates, conversion, network properties as well as degradation experiments of those thiol monomers in combination with triallyl‐1,3,5‐triazine‐2,4,6(1H,3H,5H)‐trione (TATT) as ene component were performed and compared with formulations containing the commercially available mercaptopropionic ester‐based thiol pentaerythritol tetra‐3‐mercaptopropionate. Kinetic analysis revealed appropriate reaction rates and conversions reaching 90% and higher. Importantly, storage stability tests of those formulations clearly indicate the superiority of the synthesized mercaptans compared with pentaerythritol tetra‐3‐mercaptopropionate/TATT resins. Moreover, photocured samples containing silane‐based mercaptans provide higher glass transition temperatures and withstand water storage without a significant loss in their network properties. This behavior together with the observed excellent degradation resistance of photocured silane‐based thiol/TATT formulations make these multifunctional mercaptans interesting candidates for high‐performance applications, such as dental restoratives and automotive resins. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 418–424

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“…Recently, it has been shown that the mechanics of the flexible step-growth polymer backbone containing soft sulfide linkages can be enhanced significantly in poly(thioether) networks by eliminating the presence of esters [30–33]. Achieving that, and combining other benefits of step-growth processes has led us toward revisiting the thiol-ene concept for dental composite applications.…”

Section: Introductionmentioning

confidence: 99%

Ester-free thiol–ene dental restoratives—Part B: Composite development

et al. 2015

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Objectives To assess the performance of thiol-ene dental composites based on selected ester-free thiol-ene formulations. Further, to point out the benefits/drawback of having a hydrolytically stable thiol-ene matrix within a glass filled composite. Methods Composite samples containing 50–65 wt% of functionalized glass microparticles were prepared and photopolymerized in the presence of a suitable visible light photoinitiator. Shrinkage stress measurements were conducted as a function of the irradiation time. Degrees of conversion were measured by FT-IR analysis by comparing the double bond signals before and after photopolymerization. Mechanical tests were carried out on specimens after curing as well as after extended aging in water. Dynamic mechanical analysis was employed to track the changes in storage modulus near body temperature. The properties of the thiol-ene composites were compared with those of the BisGMA/TEGDMA control. Results Depending on the resin type, similar or higher conversions were achieved in thiol-ene composites when compared to the dimethacrylate controls. At comparable conversions, lower shrinkage stress values were achieved. Although exhibiting lower initial elastic moduli, the thiol-ene composite’s flexural strengths were found to be comparable with the controls. Contrary to the control, the mechanical properties of the ester-free thiol-ene composites were shown to be unaffected by extensive aging in water and at least equaled that of the control after aging in water for just five weeks. Significance Employing non-degradable step-growth networks as organic matrices in dental composites will provide structurally uniform, tough materials with extended service time.

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Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

Cited by 19 publications

References 36 publications

Ester-free thiol-X resins: new materials with enhanced mechanical behavior and solvent resistance

Ester-free thiol-X resins: new materials with enhanced mechanical behavior and solvent resistance

Silicon‐based mercaptans: High‐performance monomers for thiol‐ene photopolymerization

Ester-free thiol–ene dental restoratives—Part B: Composite development

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