The structure of acylated chitosan derivatives strongly determines the properties of obtained products, influencing their hydrodynamic properties and thereby their solubility or self-assembly susceptibility. In the present work, the significance of slight changes in acylation conditions on the structure and properties of the products is discussed. A series of chitosan-acylated derivatives was synthesized by varying reaction conditions in a two-step process. As reaction media, two diluted acid solutions—i.e., acetic acid and hydrochloric acid)—and two coupling systems—i.e., 1-ethyl-3-(3-dimethyl-aminopropyl)-1-carbodiimide hydrochloride (EDC) and N–hydroxysulfosuccinimide (EDC/NHS)—were used. The chemical structure of the derivatives was studied in detail by means of two spectroscopic methods, namely infrared and nuclear magnetic resonance spectroscopy, in order to analyze the preference of the systems towards N- or O-acylation reactions, depending on the synthesis conditions used. The results obtained from advanced 1H-13C HMQC spectra emphasized the challenge of achieving a selective acylation reaction path. Additionally, the study of the molecular weight and solution behavior of the derivatives revealed that even slight changes in their chemical structure have an important influence on their final properties. Therefore, an exact knowledge of the obtained structure of derivatives is essential to achieve reaction reproducibility and to target the application.
An efficient synthesis of bromofunctionalized 2,6-methano- and 1,5-methano-benzomorphanones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, is described. Furthermore, the synthesis of bridged benzomorphanones with hitherto not known polycyclic systems containing 2- or 3-azabicyclo[4.1.0]heptane units is developed upon treatment of both 2,6- and 1,5-methanobromobenzomorphans with t-BuOK. The effects of substituents on the diversity and stereoselectivity of both transformations are studied.
The aim of this work was to investigate the thermal and mechanical properties of novel, electron beam-modified ester elastomers containing multifunctional alcohols. Polymers tested in this work consist of two blocks: sebacic acid–butylene glycol block and sebacic acid–sugar alcohol block. Different sugar alcohols were utilized in the polymer synthesis: glycerol, sorbitol, xylitol, erythritol, and mannitol. The polymers have undergone an irradiation procedure. The materials were irradiated with doses of 50 kGy, 100 kGy, and 150 kGy. The expected effect of using ionizing radiation was crosslinking process and improvement of the mechanical properties. Additionally, a beneficial side effect of the irradiation process is sterilization of the affected materials. It is also worth noting that the materials described in this paper do not require either sensitizers or cross-linking agent in order to perform radiation modification. Radiation-modified poly(polyol sebacate-co-butylene sebacate) elastomers have been characterized in respect to the mechanical properties (quasi-static tensile tests), cross-link density, thermal properties (Differential Scanning Calorimetry (DSC)), chemical properties: Fourier transform infrared spectroscopy (FTIR), and wettability (water contact angle). Poly(polyol sebacate-co-butylene sebacate) preopolymers were characterized with nuclear magnetic resonance spectroscopy (1H NMR and 13C NMR) and gel permeation chromatography (GPC). Thermal stability of cross-linked materials (directly after synthesis process) was tested with thermogravimetric analysis (TGA).
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