Acrylic bone cements: Residuals and extractability of methacrylate monomers and aromatic amines

Abstract

A new formulation of acrylic bone cement [methylmethacrylateln-decylmethacrylate/ isobornylmethacrylate (MMA/DMA/IBMA)] developed with the purpose of reducing the biologic adverse effects of bone cements was analyzed by high performance liquid chromatography for residual content of monomers and aromatic amines from the accelerator system [dimethyl-p-toluidine (DMPT), dihydroxypropyl-p-toluidine (DHPPT)] in the cured cement and for concentrations of these constituents in hydrophilic and lipophilic eluates. In comparison with conventional polymethyl-methacrylate acrylics a considerable reduction of both released and residual MMA was experienced, being about 10-to 15-fold. The residual content of the new DMA and IBMA monomers were 0.35% and 0.66%, respectively, in cured cement after 72 h and these could only be detected in the paraffin eluates. The residual content of aromatic amines was considerably reduced with the new cement formulation. No DMPT could be detected and the DHPPT represented a 3-to 4-fold reduction in cured cement and a 8-to 10-fold reduction in eluates. The residual DHPPT content of about 0.07% was found to be practically constant with time. It is concluded that MMA/ DMA/IBMA cement cures faster and more completely.

Application of long chain amine activator in conventional acrylic bone cement

“…4,5 Boesch and coworkers 6 reported the presence of unreacted DMT (0.5-0.71%) in cements implanted over Acrylic bone cements are generally obtained by free radical periods of 2 to 10 years. Although the toxicity data on polymerization of methyl methacrylate (MMA) monomer DMT is scarce in the literature, 4,5,7 it is considered to be a in the presence of a solid phase consisting of poly(methyl highly toxic compound by inhalation and ingestion. Due methacrylate) (PMMA).…”

Role of amine activators on the curing parameters, properties and toxicity of acrylic bone cements

“…The methacryloyl derivative seemed to produce materials with accelerated ageing and less satisfactory mechanical properties when compared to the corresponding acryloyl derivatives. Trap et al 8 have developed a new bone cement (Boneloc) which contains dihydroxypropyl-4-toluidine as the activator. The new cement cured faster and more completely than the conventional Palacos R or Simplex RO.…”

Biocompatibility and other properties of acrylic bone cements prepared with antiseptic activators

“…3 Boesch et al 4 reported the presence of DMT in quantities ranging from 0.05 to 0.71% in PMMA cements implanted for 2.5-10 years. Other studies 2,5,6 reported an average content of tertiary aromatic amines in the cured acrylic bone cements of 0.1-0.5 wt.%. On the other hand, tertiary aromatic amines are lowmolecular-weight compounds, which may leach out from the acrylic cement to the surrounding tissues.…”

“…On the other hand, tertiary aromatic amines are lowmolecular-weight compounds, which may leach out from the acrylic cement to the surrounding tissues. 2,6 Stea et al 7 analyzed the release of DMT by high-performance liquid chromatography and demonstrated that there is a correlation between the amount of DMT released and the cytotoxic effects on the cell replication. Replication cycle is inhibited in short periods of time; however, DMT toxicity on cell cultures seems to be reversible and the cells do not die, but undergo a slackening in their replication cycle.…”

“…1 Commercially available formulations of acrylic bone cements usually contain the N,N-dimethyl-4-toluidine (DMT) in a concentration range of 1.5-2.5 wt.% as an activator in the polymerization of the methyl methacrylate monomer initiated by benzoyl peroxide (BPO). 2 The toxicity of the amine/BPO initiation system is related to the mobility of the amine if other compounds are essentially nontoxic. The presence of the tertiary amine DMT is known to exist in small quantities in cured cements even after long-term storage in air or postimplantation.…”