Synthesis of Di- and Triacrylamides with Tertiary Amine Cores and Their Evaluation as Monomers in Dental Adhesive Interfaces

Fugolin, Ana Paula Piovezan; Navarro, Oscar; Logan, Matthew G.; Huynh, Vincent; França, Cristiane Miranda; Ferracane, Jack L.; Pfeifer, Carmem S.

doi:10.2139/ssrn.3600451

Cited by 3 publications

(9 citation statements)

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“…Overall, the adhesive type significantly affected gap formation, with the acrylamide-based materials producing narrower and fewer gaps overall, though the initial width is not affected (Appendix Tables 3 and 4 show gap increase calculations). This agrees with a previous study demonstrating more stable bond strengths after 6 mo with the use of this monomer, in spite of decreased adhesive bulk mechanical properties in water (Fugolin, Navarro, et al 2020). Several factors may be at play here, such as the much greater stability of the methacrylamide monomers in acidic environments (Fugolin, Logan, et al 2021) and potentially some MMP inhibition and collagen crosslinking, which have both been demonstrated with amide-based compounds (Ayoup et al 2020).…”

Section: Discussionsupporting

confidence: 93%

“…Other factors, such as the mono- vs. multifunctional nature of each monomer, as well as their intrinsic flexibility, likely played more prominent roles to determine the final conversion. Solvents were not added to the materials for the kinetics experiments, so the conversion results might not exactly correlate with what was observed when polymerizing on the dentin substrate in the presence of solvents, as previously demonstrated (Fugolin, Navarro, et al 2020). The TMAAEA-based adhesives produced statistically higher MTBS when compared with HEMA-based adhesives in all storage periods.…”

Section: Discussionmentioning

confidence: 97%

“…Combined, these methods demonstrate that restorations made with the triacrylamide-based adhesive, combined or not with the TU-containing composite, produce smaller gap sizes, especially in the simulated physiologic situation (bioreactor + bacteria). This is explained by the lower degradation of the acrylamide bonds in acidic environments (Fugolin, Navarro, et al 2020) and the potential for MMP inhibition and collagen crosslinking by amide compounds (Ayoup et al 2020), as mentioned. It is possible that the reduced polymerization stress afforded by the TU (Bacchi et al 2014) provided some protection to the interface, though this has not influenced the initial gap.…”

Section: Discussionmentioning

confidence: 99%

“…Those failures were not considered in the averages shown in the graph, so these results are likely overestimated. Evidently, even though a correlation between the 2 factors has been established (Hasegawa et al 2021), the conversion alone does not explain the MTBS results, especially in light of the significant reduction in mechanical properties demonstrated for these acrylamides after 7-d storage in water (Fugolin, Navarro, et al 2020). Therefore, other mechanisms must be at play to explain the maintenance of the bond strength even after the severe biofilm challenge, which destroyed most specimens made with the HEMA-based material.…”

Section: Discussionmentioning

confidence: 99%

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Triacrylamide-Based Adhesives Stabilize Bonds in Physiologic Conditions

et al. 2022

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In this study, an acrylamide-based adhesive was combined with a thiourethane-based composite to improve bond stability and reduce polymerization stress, respectively, of simulated composite restorations. The stability testing was conducted under physiologic conditions, combining mechanical and bacterial challenges. Urethane dimethacrylate was combined with a newly synthesized triacrylamide (TMAAEA) or HEMA (2-hydroxyethyl-methacrylate; control) to produce a 2-step total-etch adhesive system. Methacrylate-based composites (70 wt% silanized filler) were formulated, containing thiourethane oligomers at 0 (control) or 20 wt%. Standardized preparations in human third molars were restored; then, epoxy replicas were obtained from the occlusal surfaces before and after 7-d storage in water or with Streptococcus mutans biofilm, which was tested after storage in an incubator (static) or the bioreactor (mechanical challenge). Images were obtained from the replicas (scanning electron microscopy) and cross sections of the samples (confocal laser scanning microscopy) and then analyzed to obtain measurements of gap, bacterial infiltration, and demineralization. Microtensile bond strength of specimens stored in water or biofilm was assessed in 1-mm2 stick specimens. Data were analyzed with analysis of variance and Tukey’s test (α = 0.05). HEMA-based materials had greater initial gap measurements, indicating more efficient bonding for the acrylamide materials. When tested in water, the triacrylamide-based adhesive had smaller gaps in the incubator or bioreactor. In the presence of biofilm, there was less difference among materials, but the acrylamide/thiourethane combination led to statistically lower gap formation in the bioreactor. HEMA and TMAAEA-based adhesives produced statistically similar microtensile bond strengths after being stored in water for 7 d, but after the same period with biofilm-challenged specimens, the TMAAEA-based adhesives were the only ones to retain the initial bond strength values. The use of a stable multiacrylamide-based adhesive led to the preservation of the resin-dentin bonded interface after a physiologically relevant challenge. Future studies will include a multispecies biofilm model.

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Section: Discussionsupporting

confidence: 93%

Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Triacrylamide-Based Adhesives Stabilize Bonds in Physiologic Conditions

et al. 2022

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“…Incorporation of AAM into adhesive can improve its mechanical properties. For example, Rodrigues et al reported an experimental adhesive resin containing hydroxyethyl acrylamide used for dental adhesive resin, which showed that the addition of acrylamide not only increased the material′s reactivity, but also improved the mechanical properties of dental adhesive resin [38,39].…”

Section: Introductionmentioning

confidence: 99%

Highly stretchable, compressible, adhesive hydrogels with double network

Guo

Zeng

et al. 2021

J Polym Res

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In this work, a double network bovine serum albumin-polyacrylamide (BSA-PAM) adhesive hydrogel was fabricated, in which combination of physical interactions including hydrogen bonds and chain entanglements, and chemical covalent photo-crosslinking. The BSA-PAM hydrogel exhibited excellent mechanical and adhesive properties. The composite hydrogel not only demonstrated excellent tensile properties (maximum force elongation 1552%~2037%), but also displayed extremely high fatigue resistance even when subjected to compress strains of up to 85%. More importantly, the BSA-PAM hydrogel showed excellent adhesiveness to various substrates (90 kPa~150 kPa for glass and 9.74 kPa~35.09 kPa for pigskin). This work provided a facile way of fabricating tough, stretchable and adhesive BSA-PAM hydrogels.

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Progress in Dental Adhesive Materials

et al. 2023

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There have been significant advances in adhesive dentistry in recent decades, with efforts being made to improve the mechanical and bonding properties of resin-based dental adhesive materials. Various attempts have been made to achieve versatility, introducing functional monomers and silanes into the materials’ composition to enable the chemical reaction with tooth structure and restorative materials and a multimode use. The novel adhesive materials also tend to be simpler in terms of clinical use, requiring reduced number of steps, making them less technique sensitive. However, these materials must also be reliable and have a long-lasting bond with different substrates. In order to fulfill these arduous tasks, different chemical constituents and different techniques are continuously being developed and introduced into dental adhesive materials. This critical review aims to discuss the concepts behind novel monomers, bioactive molecules, and alternative techniques recently implemented in adhesive dentistry. Incorporating monomers that are more resistant to hydrolytic degradation and functional monomers that enhance the micromechanical retention and improve chemical interactions between adhesive resin materials and various substrates improved the performance of adhesive materials. The current trend is to blend bioactive molecules into adhesive materials to enhance the mechanical properties and prevent endogenous enzymatic degradation of the dental substrate, thus ensuring the longevity of resin–dentin bonds. Moreover, alternative etching materials and techniques have been developed to address the drawbacks of phosphoric acid dentin etching. Altogether, we are witnessing a dynamic era in adhesive dentistry, with advancements aiming to bring us closer to simple and reliable bonding. However, simplification and novelty should not be achieved at the expense of material properties.

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Synthesis of Di- and Triacrylamides with Tertiary Amine Cores and Their Evaluation as Monomers in Dental Adhesive Interfaces

Cited by 3 publications

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Triacrylamide-Based Adhesives Stabilize Bonds in Physiologic Conditions

Triacrylamide-Based Adhesives Stabilize Bonds in Physiologic Conditions

Highly stretchable, compressible, adhesive hydrogels with double network

Progress in Dental Adhesive Materials

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