Poly(methyl methacrylate) denture base materials modified with ditetrahydrofurfuryl itaconate: Significant applicative properties

Abstract

The aim of this work was to examine the possibility of modification of commercial denture base materials with itaconic acid esters, in order to obtain material with less toxicity and higher biocompatibility. Despite their relatively higher price compared to methacrylates, itaconic acid and itaconates are materials of choice for environmentally friendly applications, because they are not produced from petrochemical sources, but from plants. Commercial system based on poly(methyl methacrylate) was modified using ditetrahydrofurfuryl itaconate (DTHFI), wherein the ratio of DTHFI was varied from 2.5 to 10% by weight. Copolymerization was confirmed using FTIR spectroscopy, while SEM analysis showed the absence of micro defects and pores in the structure. The effect of the itaconate content on the absorption of fluids, the residual monomer content, thermal, dynamic-mechanical and mechanical properties (hardness, toughness, stress and elongation at break) was investigated. It was found that the addition of DTHFI significantly reduced the amount of residual methyl methacrylate, what made these materials less toxic. It was shown that the increase in DTHFI content gave materials with decreased glass transition temperature, as well as with decreased storage modulus, ultimate tensile strength and impact fracture resistance, however mechanical properties were in the rang prescribed by ADA standards, and can be used in practice. The deterioration of mechanical properties was therefore worth losing in order to gain lesser toxicity of the leached monomer. [Projekat Ministarstva nauke Republike Srbije, br. 172062: Synthesis and characterization of novel functional polymers and polymeric nanomaterials]

Monomer modifications of denture base acrylic resin: A systematic review and meta-analysis

“…From the included researches in the systematic review, the modification of MMA was done basically by certain monomers or solutions that can be categorized as fluoromonomers[2627282930] ( n = 5), phosphate monomers[313233] ( n = 3), methacrylic acid monomer[343536373839] ( n = 6), itaconate monomers[404142] ( n = 3), nitromonomers[543444546] ( n = 5), and nonspecific monomers or solutions ( n = 6). Nonspecific monomers include Norbonyl/phenyl methacrylate (NBMA/PHMA),[47] polyhedral oligosilsesquioxane (POSS),[48] methacrylated dendrimer (DD1),[49] 1,3-bis(3-methacryloxypropyl)-1,1,3,3 tetramethyl disiloxane (BMPMS),[50] silver nitrate (AgNO 3 ) solution,[51] and N -acetyl cysteine (NAC).…”

“…The monomers used to substitute with MMA (wt/vol%) were either experimentally synthesized[33424445474951] or purchased. [526272829303234353637383940414346485052] For the specimen preparation, the polymer beads were synthesized by bulk polymerization,[29474950] suspension polymerization,[2627283334] or from the commercially available pre-polymers.…”

The influence of the shape and size of the AL2O3 particles on the flexural properties of the PMMA composite modified by the addition of dimethyl itaconate

“…Utvrđeno je da dodatak dietil itakonata u PMMA značajno smanjuje količinu zaostalog monomera (metil metakrilata), što čini ove materijale manje toksičnim. S druge strane, smanjena količina zaostalog monomera dovodi do pogoršanja mehaničkih svojstava materijala [14].…”

Dimethyl Itaconate Modified PMMA ‐ Alumina Fillers Composites With Improved Mechanical Properties

“…It is important to note that itaconates have been extensively used in varying medical applications because of their very low toxicity . In our previous studies, we found that the addition of itaconate derivate to PMMA denture base materials decreases the content of residual methyl methacrylate (MMA) . This was explained by the fact that the methacrylates are more reactive than the itaconates due to the steric hindrance of the alkyl group .…”

“…This was explained by the fact that the methacrylates are more reactive than the itaconates due to the steric hindrance of the alkyl group . Thus, as the copolymerization progress MMA is faster depleted, leading to the significantly lower concentration of the MMA at the end of the reaction . However, the total residual monomer (TRM) concentration was higher compared with the composition containing only MMA.…”