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Abstract Alcoholysis is a promising approach for upcycling postconsumer polylactide (PLA) products into valuable constituents. In addition, an alcohol-acidolysis of PLA by multifunctional 2,2-bis(hydroxymethyl)propionic acid (DMPA) produces lactate oligomers with hydroxyl and carboxylic acid terminals. In this work, a process for sizing down commercial PLA resin to optimum medium-sized lactate oligomers is developed at a lower cost than a bottom-up synthesis from its monomer. The microwave-assisted reaction is conveniently conducted at 220–240 °C and pressure lower than 100 psi. The PLA resin was completely converted via alcohol-acidolysis reaction, with a product purification yield as high as 93%. The resulting products are characterized by FTIR, 2D-NMR, 1H-NMR, GPC, DSC, and XRD spectroscopy. The effects of PLA: DMPA feed ratios and the incorporation of 1,4-butanediol (BDO) on the structures, properties, and particle formability of the alcohol-acidolyzed products are examined. The products from a ratio of 12:1, which possessed optimum size and structures, are used to synthesize PLA-based polyurethane (PUD) by reacting with 1,6-diisocyanatohexane (HDI). The resulting PUD is employed in encapsulating lavender essential oil (LO). Without using any surfactant, stable LO-loaded nanoparticles are prepared due to the copolymer’s self-stabilizability from its carboxylate groups. The effect of the polymer: LO feed ratio (1.25–3.75: 1) on the physicochemical properties of the resulting nanoparticles, e.g., colloidal stability (zeta potential > -60 mV), hydrodynamic size (300–500 nm), encapsulation efficiency (80–88%), and in vitro release, are investigated. The LO-loaded nanoparticles show non-toxicity to fibroblast cells, with an IC50 value higher than 2000 µg/mL. The products from this process have high potential as drug encapsulation templates in biomedical applications.

Abstract Stimuli-responsive controlled delivery systems are of interest for preventing premature leakages and ensuring precise releases of active compounds at target sites. In this study, porous biodegradable micro/nanoparticles embedded with thermoresponsive gatekeepers are designed and developed based on Eudragit RS100 (PNIPAM@RS100) and poly(N-isopropylacrylamide) via a double emulsion solvent evaporation technique. The effect of initiator types on the polymerization of NIPAM monomer/methylene-bis-acrylamide (MBA) crosslinker was investigated at 60 °C for thermal initiators and ambient temperature for redox initiators. The crosslinked PNIPAM plays a key role as thermal-triggered gatekeepers with high loading efficiency and precise release of a model active compound, Nile Blue A (NB). Below the volume phase transition temperature (TVPT), the gatekeepers possess a swollen conformation to block the pores and store NB within the cavities. Above its TVPT, the chains rearrange, allowing gate opening and a rapid and constant release rate of the compound until completion. A precise “on–off” switchable release efficiency of PNIPAM@RS100 was demonstrated by changing the temperatures to 4 and 40 °C. The materials are a promising candidate for controlled drug delivery systems with a precise and easy triggering mechanism at the body temperature for effective treatments.