Synthesis of new photoactive urethane carbohydrates and their behavior in UV or femtosecond laser-induced two-photon polymerization

Abstract

Three methacrylated glycomonomers (CMA-1–3) were synthesized, characterized, and photocrosslinked in hydrophilic conetworks. The UV photobehavior of monomers was evaluated through FTIR spectrometry using Irgacure 819/Irgacure 2959 as photoinitiator, and the results showed that Irgacure 2959 is a better photoinitiator, the conversion degree (DC) varying in the range of 69–89.2% and the maximum rate of polymerization () being ~10 s⁻¹. The addition of poly(ethylene glycol) dimethacrylate (PEG-DMA) or benzophenone macromer (BP-UDMA) as co-monomer improved the and DC (up to 100% after 300 s of irradiation in the latter). Specific analysis (gel fraction, water uptake, morphology) of the photopolymerized networks A1–A3 (CMA-1–3/PEG-DMA) and B1–B3 (CMA-1–3/BP-UDMA) demonstrated that B1–B3 films have interconnected inner pores, with irregular shapes and different sizes. The grid structures created through the two-photon polymerization of B1–B3 formulations in the presence of Irg819 are clearer and have a controlled porosity, of relevance for promising bioapplications.

Keywords:

• Urethane glyco-methacrylates
• UV photopolymerization
• α-d-glucofuranose
• α-d-galactopyranose
• d-mannitol

Acknowledgments

A. L. Chibac is thankful for the financial support offered by European Social Fond – ‘Doctoral and postdoctoral programs – support for increasing research competitiveness in the field of Exact Sciences’ – ID POSDRU/159/1.5/S/137750, Sectorial Operational Programme Human Resources Development.

The authors E. C. Buruiana, T. Buruiana and G. Epurescu are thankful for the financial support offered by CNCSIS-UEFISCDI, project number PN-II-PT-PCCA-2011-3.1-1422 (146/2012).

Funding

This work was financially supported by the European Social Fond – ‘Doctoral and postdoctoral programs – support for increasing research competitiveness in the field of Exact Sciences’ [grant number ID POSDRU/159/1.5/S/137750]; CNCSIS-UEFISCDI [grant number PN-II-PT-PCCA-2011-3.1-1422 (146/2012)].

Disclosure statement

No potential conflict of interest was reported by the authors.