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Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

ABSTRACT: 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.

SUBMITTER: Podgorski M

PROVIDER: S-EPMC4397656 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

Podgórski Maciej M Becka Eftalda E Chatani Shunsuke S Claudino Mauro M Bowman Christopher N CN

Polymer chemistry 20150101 12

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, mercaptopro ...[more]

PMID: 25893009

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Project description:Organophosphazenes are of interest due to the combination of increased mechanical and thermal properties of polymer materials obtained with their use, however, they are characterized by a complex multi-stage synthesis. Moreover, the high viscosity of phosphazene-containing epoxy resins (PhER) makes their processing difficult. To simplify the synthesis of PhER, a one-step method was developed, and bisphenol F was chosen, which also provided a decrease in viscosity. In the current study, PhER were formed by a one-stage interaction of hexachlorocyclotriphosphazene (HCP) with bisphenol F isomers and epichlorohydrin in the presence of alkali, which was a mixture of epoxycyclophosphazenes (ECPh) with a functionality from 1 to 4 according to the results of MALDI-TOF analysis. Conventional epoxy resins based on bisphenol F, also formed during the process, showed high mechanical properties and glass transition temperature, and the reactivity of the obtained resins is similar to the base epoxy resins based on bisphenols A and F. Cured PhER had higher or the same mechanical properties compared to base epoxy resins based on bisphenol A and F, and a glass transition temperature comparable to base epoxy resins based on bisphenol F: glass transition temperature (Tg) up to 174.5 °C, tensile strength up to 74.5 MPa, tensile modulus up to 2050 MPa, tensile elongation at break up to 6.22%, flexural strength up to 146.6 MPa, flexural modulus up to 3630 MPa, flexural elongation at break up to 9.15%, and Izod impact strength up to 4.01 kJ/m2. Analysis of the composition of the obtained PhER was carried out by 1H and 31P NMR spectroscopy, MALDI-TOF mass spectrometry, X-ray fluorescence elemental analysis, and contained up to 3.9% phosphorus and from 1.3% to 4.2% chlorine. The temperature profile of the viscosity of the resulting epoxy resins was determined, and the viscosity at 25 °C ranged from 20,000 to 450,000 Pa·s, depending on the ratio of reagents. The resins studied in this work can be cured with conventional curing agents and, with a low content of the phosphazene fraction, can act as modifiers for traditional epoxy resins, being compatible with them, to increase impact strength and elasticity while maintaining the rest of the main mechanical and processing properties, and can be used as a resin component for composite materials, adhesives, and paints.

Project description:OBJECTIVES:Quaternary ammonium (QA) methacrylate monomers have been extensively investigated and demonstrate excellent antibacterial properties. However, the presence of ester bonds makes them prone to degradation in the oral cavity. In this study, ester-free QA monomers based on meth-acrylamides were synthesized and screened for polymerization kinetics, mechanical properties and antibacterial effects. MATERIALS AND METHODS:Tertiary quaternary ammonium acrylamides (AM) and methacrylamides (MAM) with alkyl side chain lengths of 9 and 14 carbons (C9 and C14) were synthesized and incorporated at 10 wt% into experimental composites based on BisGMA:TEGDMA (1:1), camphorquinone/ethyl-4-dimethylaminobenzoate (0.2/0.8 wt%) and 70 wt% barium glass fillers. Analogous methacrylate versions (MA) were used as controls. Degree of conversion (DC) and rate of polymerization (RP) during photoactivation (800 mW/cm2) were followed in real-time with near-IR. Flexural Strength (FS) and Modulus (E) were measured on 2 × 2 × 25 mm bars in 3-point bending after 24 h dry storage and 7-day storage in water at 37 °C. Antimicrobial properties and biofilm adhesion (fouling) were evaluated by bioluminescence (Luciferase Assay) and biofilm removal by water spray microjet impingement test, respectively. Cytotoxicity was assessed by MTT assay on dental pulp stem cells (DPSC). Data were analyzed with one-way ANOVA/Tukey's test (α = 0.05). RESULTS:DC was similar for all groups tested (∼70%). Both MAMs and C14-AM presented significantly lower RP. Under dry conditions, FS (110-120 MPa) and E (8-9 GPa) were similar for all groups. After water storage, all materials presented FS/E similar to the control, except for C14-AM (for FS) and C14-MAM (for E), which were lower. All C14 versions were strongly antibacterial, decreasing the titer counts of biofilm by more than two orders of magnitude in comparison to the control. C9 monomers did not present significant antibacterial nor antifouling properties. And biofilms had approximately equivalent adhesion on the C9 composites as on the control. Cytotoxicity did not show significant differences between the MA and AM versions and the control group. CONCLUSIONS:C14-QA monomers based on methacrylates and meth-acrylamides present strong antibacterial properties, and in general, similar conversion/mechanical properties compared to the methacrylate control. STATEMENT OF SIGNIFICANCE:This work demonstrates the viability of methacrylamides and acrylamides as potential components in dental restorative materials with antimicrobial properties. The use of ester-free polymerizable functionalities has the potential of improving the degradation resistance of these materials long-term. The use of (meth)acrylamides did not interfere with the antimicrobial potential of quaternary ammonium-based materials.

Dataset Information

Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

Publications

Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

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