Catalyst Selection for Body-Temperature Curable Polyurethane Networks from Poly(δ-Decalactone) and Lysine Diisocyanate

With aging, harsh working conditions or sports injuries, the meniscus can degrade, causing pains to the patient. Nowadays, the treatment consists of the surgical replacement of this cartilage. Since this procedure can lead to complications due to open wounds and potential infections, synthesizing a polyurethane-based injectable joint filler represents an interesting alternative. In this study, poly(δ-decalactone)triol oligomers and Lysine diisocyanate were chosen as starting monomers to create an isocyanate-based prepolymer, because of their biocompatibility and liquid state at room temperature. Nevertheless, to fully replace the meniscus, the joint filler must crosslink in vivo, and this should occur in a short time window. Accordingly, in this work, we studied the catalytic activity of a range of relatively safe compounds for the alcohol/isocyanate addition reaction. A preliminary ¹H NMR kinetic study of the catalyzed addition of 1-butanol or 3-pentanol on lysine diisocyanate ethyl ester at body temperature has been performed to reach this objective. Among catalysts, stannous octoate was the most effective with either primary or secondary alcohol, allowing them to reach 92 and 80% alcohol conversion, respectively. In addition, the conversion of the primary and secondary isocyanates of lysine diisocyanate ethyl ester was monitored for all the catalysts and revealed different behaviors depending on the catalyst employed. Stannous octoate, unlike the others, showed a similar reactivity for primary and secondary isocyanates with conversions of 49 and 47%, respectively. Finally, when employing the most effective catalyst, curing of the poly(δ-decalactone) triisocyanate with glycerol at 35 °C provided a polyurethane elastomer that exhibits an elastic modulus of 519 kPa and a swelling index lower than 3% in PBS, making it suitable for injectable polyurethane joint filler application.