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Oak bark is a by-product known for its richness in polyphenols, with tanning substances being particularly interesting for their application in different fields. Vegetable tannins are mostly utilized in the leather sector, but are also widely used as adhesives, in cement plasticizers and for medical and agrochemical applications owing to their natural antimicrobial activity. This study aimed to develop a green and efficient pilot-scale technique for extracting polyphenols from oak bark by ultrasound-assisted extraction (UAE) using a modified Dual-Frequency Reactor (DFR). Different parameters, such as extraction time, temperature, and solvent type (water, sodium hydroxide or sodium sulfite and bisulfite solutions) were investigated for their influence on the total phenolic content (TPC) and the quantity of dry extract. Control experiments by conventional methods were also performed. UAE at 50 °C yielded the highest TPC and dry extract (confirmed by ANOVA analysis, p < 0.05) in just 10 min, suggesting that UAE can be considered an energy- and cost-effective alternative to conventional techniques. The most suitable solvent was found to be a 0.5% sodium hydroxide solution. The molecular profile of the extracts was assessed by FTIR-ATR spectroscopy, revealing typical signals of tannins in all extracts. Furthermore, antimicrobial activity tests demonstrated the complete absence of Gram-positive and Gram-negative bacteria in the extracts, ensuring the suitability of the product for different kinds of application.

Sustainability of leather lies in how the hide, a sustainable, naturally renewable, raw material, is processed. Tanning chemistry has been a limiting factor for leather sustainability. In this study, a host-guest synthesis strategy was selected to modify one of the most widely used tanning polymer, MIDA DD, and obtain a new hybrid tanning system containing β-cyclodextrin, and leather drastically less impactful on the earth and people. Poly[2]pseudorotaxane Side-Chain Complexes (PSCCs) have been obtained by threading β-cyclodextrin units onto the side-chains of the commercial MIDA DD. The formation of PSCCs in aqueous solution was investigated by using 1D NMR, ATR-FTIR and TGA experiments. The ability of PSCCs to stabilize the collagen matrix was tested at laboratory and industrial pilot scale by micro-DSC, ATR-FTIR and solid-state NMR techniques. The physical and mechanical performance of the obtained crust leather was determined by standard tests used in tanning industry. Side-chain poly[2]pseudorotaxanes showed better tanning performances than the fossil-based MIDA DD, the most effective supramolecular tannins being obtained by mixing β-CD and MIDA DD in ratios close to 1/1 (w/w). The new tanning mixtures allow for significantly reducing both the amount of fossil-based MIDA-DD polymer in the current tanning processes (by 45%) and the free bisphenol content in leather crust (by more than 80%) due to the presence of bio-based β-CD in the composition of the new supramolecular tanning agents. The findings disclosed here pave the way for the CDs’ employment in improving the sustainability of tanning processes.