Novel lignin α-O-4 derived hydrogen donors in CQ-based photoinitiating systems for dental resins.
Amine-free
Dental resin
Hydrogen donor
Lignin α-O-4
Photo-initiating system
Photopolymerization
Journal
Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288
Informations de publication
Date de publication:
19 Jul 2024
19 Jul 2024
Historique:
received:
14
03
2024
accepted:
10
07
2024
medline:
20
7
2024
pubmed:
20
7
2024
entrez:
19
7
2024
Statut:
epublish
Résumé
The purpose of this work is to explore the properties of the lignin-derived amine-free photoinitiating systems (PISs) during the curing process. Four novel hydrogen donors (HD1, HD2, HD3, and HD4) derived from lignin α-O-4 structural were designed and synthesized by simple methods, and their low C-H bond dissociation energies on methylene were determined by molecular orbitals theory. Four experimental groups using CQ (camphorquinone)/HD PIs formulated with Bis-GMA/TEGDMA (70 w%/30 w%) were compared to CQ/EDB (ethyl 4-dimethylamino benzoate) system. The photopolymerization profiles and double bond conversion rate was tracked by FTIR experiments; the color bleaching ability of the samples and color aging test assay were performed using color indexes measurements; The cytotoxicity of the samples was also compared to EDB related systems. All of the experimental groups with new HDs were compared to the control group with EDB by statistical analysis. Compared to CQ/EDB system, new lignin-derived hydrogen donors combined with CQ showed comparable or even better performances in polymerization initiation to form resin samples, under a blue dental LED in air. Excellent color bleaching property was observed with the new HDs. Aging tests and cytotoxicity examination of the resin were performed, indicating the new lignin compounds to be efficient hydrogen donors for amine-free CQ-based photo-initiating system. Novel lignin α-O-4 derived hydrogen donors are promising for further usage in light-curing materials.
Identifiants
pubmed: 39030243
doi: 10.1038/s41598-024-67377-z
pii: 10.1038/s41598-024-67377-z
doi:
Substances chimiques
Lignin
9005-53-2
Hydrogen
7YNJ3PO35Z
camphorquinone
RAL3591W33
Terpenes
0
Resins, Synthetic
0
Dental Materials
0
Polyethylene Glycols
3WJQ0SDW1A
Polymethacrylic Acids
0
Camphor
76-22-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16719Subventions
Organisme : National Natural Science Foundation of China
ID : 22278103
Organisme : Hangzhou Biomedicine and Health Development Project
ID : 2021WJCY129
Organisme : Medical Science and Technology Project of Zhejiang Province
ID : 2021KY891
Informations de copyright
© 2024. The Author(s).
Références
Fouassier, J. P. & Lalevée, J. Experimental devices and examples of applications. In Photoinitiators for Polymer Synthesis (eds Fouassier, J. P. & Lalevée, J.) 21–34 (Wiley-VCH Verlag GmbH & Co. KGaA, 2012).
doi: 10.1002/9783527648245.ch3
Price, R. B. T. Light curing in dentistry. Dent. Clin. North Am. 61, 751–778 (2017).
doi: 10.1016/j.cden.2017.06.008
pubmed: 28886767
Cook, W. D. Photopolymerization kinetics of dimethacrylates using the camphorquinone/amine initiator system. Polymer 33, 600–609 (1992).
doi: 10.1016/0032-3861(92)90738-I
Moreira, A. G. et al. Piperonyl methacrylate: Copolymerizable coinitiator for adhesive compositions. J. Dent. 79, 31–38 (2018).
doi: 10.1016/j.jdent.2018.09.006
pubmed: 30248382
Bouzrati-Zerelli, M. et al. A low migration phosphine to overcome the oxygen inhibition in new high performance photoinitiating systems for photocurable dental type resins: Photoinitiating systems for photocurable dental resins. Polym. Int. 66, 504–511 (2017).
doi: 10.1002/pi.5262
Jakubiak, J. et al. Camphorquinone–amines photoinitating systems for the initiation of free radical polymerization. Polymer 44, 5219–5226 (2003).
doi: 10.1016/S0032-3861(03)00568-8
Lalevée, J. & Fouassier, J. P. Trends in dye photosensitized radical polymerization reactions. In Dyes and Chromophores in Polymer Science (eds Lalevée, J. & Fouassier, J. P.) 1–34 (ISTE Wilev, 2015).
doi: 10.1002/9781119006671
Rueggeberg, F. A. State-of-the-art: Dental photocuring—A review. Dent. Mater. 27, 39–52 (2011).
doi: 10.1016/j.dental.2010.10.021
pubmed: 21122903
Kirschner, J. et al. Sulfinates and sulfonates as high performance co-initiators in CQ based systems: Towards aromatic amine-free systems for dental restorative materials. Dent. Mater. 36, 187–196 (2020).
doi: 10.1016/j.dental.2019.11.020
pubmed: 31791740
Sprick, E. et al. New hydrogen donors for amine-free photoinitiating systems in dental materials. Dent. Mater. 37, 382–390 (2021).
doi: 10.1016/j.dental.2020.12.013
pubmed: 33468405
Sprick, E. et al. Design of new amines of low toxicity for efficient free radical polymerization under air. Macromol. Chem. Phys. 221, 2000211 (2020).
doi: 10.1002/macp.202000211
Sprick, E. et al. New bio-sourced hydrogen donors as high performance coinitiators and additives for CQ-based systems: Toward aromatic amine-free photoinitiating systems. Eur. Polym. J. 134, 109794 (2020).
doi: 10.1016/j.eurpolymj.2020.109794
Zakzeski, J., Bruijnincx, P. C. A., Jongerius, A. L. & Weckhuysen, B. M. The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 110, 3552–3599 (2010).
doi: 10.1021/cr900354u
pubmed: 20218547
Li, C., Zhao, X., Wang, A., Huber, G. W. & Zhang, T. Catalytic transformation of lignin for the production of chemicals and fuels. Chem. Rev. 115, 11559–11624 (2015).
doi: 10.1021/acs.chemrev.5b00155
pubmed: 26479313
Li, H. & Song, G. Paving the way for the lignin hydrogenolysis mechanism by deuterium-incorporated β-O-4 mimics. ACS Catal. 10, 12229–12238 (2020).
doi: 10.1021/acscatal.0c02339
Kong, X. et al. Critical roles of the oxygen-containing functional groups via β-O-4 lignin linkage hydrogenolysis over copper catalysts. ACS Sustain. Chem. Eng. 9, 10939–10947 (2021).
doi: 10.1021/acssuschemeng.1c03662
Pelzer, A. W. & Broadbelt, L. J. Effects of substituents on the SN2 free energy of activation for α-O-4 lignin model compounds. J. Phys. Chem. 121, 7603–7614 (2017).
Sugiarto, S., Leow, Y., Tan, C. L., Wang, G. & Kai, D. How far is lignin from being a biomedical material?. Bioact. Mater. 8, 71–94 (2022).
pubmed: 34541388
Chen, Y. et al. A metal-free synthesis of 3-phenoxyimidazo heterocycles by catalytic oxidative cyclization of 2-amino-azaarenes with lignin models. Synthesis 50, 3169–3176 (2018).
doi: 10.1055/s-0037-1610139
Luo, S. et al. Lignin-derived new hydrogen donors for photoinitiating systems in dental materials. J. Dent. 132, 104477 (2023).
doi: 10.1016/j.jdent.2023.104477
pubmed: 36914066
Zhang, C. et al. Synthesis of 3-oxo quinolines by cyclization using lignin models and 2-aminobenzyl alcohols. J. Org. Chem. 88, 3436–3450 (2023).
doi: 10.1021/acs.joc.2c02455
pubmed: 36867549
Zhang, J., Lu, X., Li, T., Wang, S. & Zhong, G. Copper-catalyzed oxidative cyclization of 2-amino-azaarenes with lignin models: Synthesis of 3-phenoxy imidazo heterocycles. J. Org. Chem. 82, 5222–5229 (2017).
doi: 10.1021/acs.joc.7b00480
pubmed: 28429945
Salvador, M. V. O. et al. Influence of different concentrations of an iodonium salt on properties of amine-free resins. Dent. Mater. 38, 1024–1029 (2022).
doi: 10.1016/j.dental.2022.04.002
pubmed: 35469675
Zhu, W., Liu, F. & He, J. Synthesis of radio-opaque methacrylate monomer and its application in visible light-curable dental resin. Adv. Polym. Technol. 37, 922–928 (2018).
doi: 10.1002/adv.21738
Wu, X. et al. Reinforcement of dental resin composite via zirconium hydroxide coating and phosphate ester monomer conditioning of nano-zirconia fillers. J. Mech. Behav. Biomed. Mater. 94, 32–41 (2019).
doi: 10.1016/j.jmbbm.2019.03.002
pubmed: 30856477
Zhao, Y. & Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06 functionals and 12 other functionals. Theor. Chem. Acc. 119, 525–525 (2008).
doi: 10.1007/s00214-007-0401-8
Ogliari, F. A., Ely, C., Petzhold, C. L., Demarco, F. F. & Piva, E. Onium salt improves the polymerization kinetics in an experimental dental adhesive resin. J. Dent. 35, 583–587 (2007).
doi: 10.1016/j.jdent.2007.04.001
pubmed: 17540492
Andrea, G. M. et al. Surface roughness and oxygen inhibited layer control in bulk-fill and conventional nanohybrid resin composites with and without polishing: In vitro study. BMC Oral Health 22, 258 (2022).
doi: 10.1186/s12903-022-02297-w