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Optimisation of Glycerol and Itaconic Anhydride Polycondensation

ABSTRACT: Glycerol polyesters have recently become objects of interest in tissue engineering. Barely known so far is poly(glycerol itaconate) (PGItc), a biocompatible, biodegradable polyester. Due to the presence of a C=C electron-acceptor moiety, it is possible to post-modify the product by Michael additions to change the properties of PGItc. Thus, using PGItc as one of the elements of cellular scaffold crosslinked in situ for bone tissue regeneration seems to be a very attractive yet unexplored solution. This work aims to optimize the synthesis of PGItc to obtain derivatives with a double bond in the side chain with the highest conversion rates. The experiments were performed with itaconic anhydride and glycerol using mathematical planning of experiments according to the Box-Behnken plan without solvent and catalyst. The input variables of the process were the ratio of the OH/COOH, temperature, and reaction time. The optimised output variables were: the degree of esterification (EDtitr), the degree of esterification calculated from the analysis of 1H NMR spectra (EDNMR), and the degree of itaconic anhydride conversion—calculation based on 13C NMR spectra (%X13CNMR). In each of statistical models, the significance of the changed synthesis parameters was determined. Optimal conditions are when OH/COOH ratio is equal to 1.5, temperature is 140 °C and time of reaction is 5 h. The higher OH/COOH ratio, temperature and longer the experiment time, the higher the value of the degree of esterification and the degree of anhydride conversion.

SUBMITTER: Kolankowski K

PROVIDER: S-EPMC9324205 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The use of lignocellulose-rich biowaste as reinforcing filler in biodegradable polymers represents a sustainable option to obtain cost-effective bio-based materials to be used for several applications. In addition, the scarce polymer-biofiller interaction can be improved by reactive functionalization of the matrix. However, the obtained biocomposites might show high thermal deformability and possibly a slow biodegradation rate. In this work, polylactic acid (PLA) was first chemically modified with itaconic anhydride, and then biocomposites containing 50 wt.% of pecan (Carya illinoinensis) nutshell (PNS) biowaste were prepared and characterized. Their physical and morphological properties were determined, along with their biodegradation behavior in soil. Moreover, the effects of two environmentally friendly physical treatments, namely ball-milling of the filler and thermal annealing on biocomposites, were assessed. Grafting increased PLA thermal-oxidative stability and crystallinity. The latter was further enhanced by the presence of PNS, achieving a 30% overall increase compared to the plain matrix. Accordingly, the biocomposites displayed mechanical properties comparable to those of the plain matrix. Thermal annealing dramatically increased the mechanical and thermomechanical properties of all materials, and the heat deflection temperature of the biocomposites dramatically increased up to 60 °C with respect to the non-annealed samples. Finally, PNS promoted PLA biodegradation, triggering the swelling of the composites under soil burial, and accelerating the removal of the polymer amorphous phase. These results highlight the potential of combining natural fillers and environmentally benign physicochemical treatments to tailor the properties of PLA biocomposites. The high biofiller content used in this work, in conjunction with the chemical and physico-mechanical treatments applied, increased the thermal, mechanical, and thermomechanical performance of PLA biocomposites while improving their biodegradation behavior. These outcomes allow for widening the application field of PLA biocomposites in those areas requiring a stiff and lightweight material with low deformability and faster biodegradability.

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Optimisation of Glycerol and Itaconic Anhydride Polycondensation

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