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Synthesis of Biobased and Hybrid Polyurethane Xerogels from Bacterial Polyester for Potential Biomedical Applications.

ABSTRACT: Organic-inorganic xerogel networks were synthesized from bacterial poly (3-hydroxybutyrate) (PHB) for potential biomedical applications. Since silane-based networks usually demonstrate increased biocompatibility and mechanical properties, siloxane groups have been added onto polyurethane (PU) architectures. In this work, a diol oligomer (oligoPHB-diol) was first prepared from bacterial poly(3-hydroxybutyrate) (PHB) with an environmentally friendly method. Then, hexamethylene diisocyanate or biobased dimeryl diisocyanate was used as diisocyanate to react with the short oligoPHB-diol for the synthesis of different NCO-terminated PU systems in a bulk process and without catalyst. Various PU systems containing increasing NCO/OH molar ratios were prepared. Siloxane precursors were then obtained after reaction of the NCO-terminated PUs with (3-aminopropyl)triethoxysilane, resulting in silane-terminated polymers. These structures were confirmed by different analytical techniques. Finally, four series of xerogels were prepared via a sol-gel process from the siloxane precursors, and their properties were evaluated depending on varying parameters such as the inorganic network crosslinking density. The final xerogels exhibited adequate properties in connection with biomedical applications such as a high in vitro degradation up to 15 wt% after 12 weeks.

SUBMITTER: Wendels S

PROVIDER: S-EPMC8659847 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:In this paper the preparation and detailed characterization of designed polyurethanes (SPURs) are reported for potential biological, biomedical and/or pharmaceutical applications. Importantly, in order to fulfill these goals all reactants and solvents used were selected according to the proposal of EUR-8 Pharmacopoeia. For the synthesis, a novel strategy was introduced and elaborated. A series of SPUR samples was prepared from poly(?-caprolactone)-diol, 1,6-hexamethylene diisocyanate and sucrose as a chain extender/crosslinking agent to obtain sucrose containing polyurethanes. In addition, the mol ratios of the sucrose were varied within an order of magnitude. The prepolymers and the products of the syntheses were investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and infrared spectroscopy (IR), respectively. It was found that the reactivity of the eight free hydroxyl groups of sucrose are different, and after curing the SPUR samples at 60 °C no free isocyanate groups can be observed. Furthermore, swelling experiments performed with various solvents of different polarities revealed that the highest degree of swelling took place in dimethyl-sulfoxide. However, low degrees of swelling were recognized in water and hexane. It is important to note that the gel contents were around 90% in all cases, which demonstrate that the crosslinking was almost complete. In addition, the kinetics of swelling were also evaluated and successfully modeled. The crosslink densities were calculated from the data of the swelling experiments by means of the Flory-Rehner equation. Unexpectedly, it was found that the crosslink density decreased with the increasing sucrose content also in line with the results obtained by relaxation modulus experiments and dynamic mechanical analysis (DMA). The Tg and Tm of SPUR samples, determined from DSC and DMA measurements, were around -57 °C and 27 °C, respectively. According to the mechanical tests the SPUR samples showed high elongation at break values, i.e., high flexibilities. Furthermore, the stress-strain curves were also modeled and discussed.

Project description:More than 23 million tonnes of lignin are produced annually in the US from wood pulping and 98% of this lignin is burnt. Therefore, creating products from lignin, such as plastics, offers an approach for obtaining sustainable materials in a circular economy. Lignin-based copolymers were synthesized using a single pot, solvent free, melt condensation reaction. The synthesis occurred in two stages. In the first stage, a biobased prepolymer consisting of butanediol (BD, 0.8-1 molar content) and a diacid (succinic (SA), adipic (AA) and suberic acids (SuA), with varying amounts of diaminobutane (DAB, 0-0.2 molar content) was heated under vacuum and monitored by Fourier transform infra-red (FTIR) spectroscopy and electrospray ionization-mass spectrometry (ESI-MS). In the second stage, prepolymer was mixed with a softwood kraft lignin (0-50 wt.%) and further reacted under vacuum at elevated temperature. Progression of the polymerization reaction was monitored using FTIR spectroscopy. The lignin-copolyester/amide properties were characterized using tensile testing, X-ray diffraction (XRD), dynamic mechanical analysis (DMA), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) techniques. Lignin co-polymer tensile (strength 0.1-2.1 MPa and modulus 2 to 338 MPa) properties were found to be influenced by the diacid chain length, lignin, and DAB contents. The lignin-copolymers were shown to be semi-crystalline polymer and have thermoplastic behavior. The SA based copolyesters/amides were relatively stiff and brittle materials while the AA based copolyesters/amides were flexible and the SuA based copolyesters/amides fell in-between. Additionally, > 30 wt.% lignin the lignin- copolyesters/amides did not exhibit melt behavior. Lignin-co-polyester/amides can be generated using green synthesis methods from biobased building blocks. The lignin- copolyesters/amides properties could be tuned based on the lignin content, DAB content and diacid chain length. This approach shows that undervalued lignin can be used in as a macromonomer in producing thermoplastic materials.

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Synthesis of Biobased and Hybrid Polyurethane Xerogels from Bacterial Polyester for Potential Biomedical Applications.

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