Physicochemical characterization of novel Schiff bases derived from developed bacterial cellulose 2,3-dialdehyde.

The synthesis of two novel Schiff's bases (cellulose-2,3-bis-[(4-methylene-amino)-benzene-sulfonamide] (5) & cellulose-2,3-bis-[(4-methylene-amino)-N-(thiazol-2-yl)-benzenesulfonamide] (6) via condensation reactions of periodate oxidized developed bacterial cellulose ODBC (2) with sulfa drugs [sulfanilamide (3) & sulfathiazole (4)] was reported. The physicochemical characterization of the condensation products was performed using FTIR, (1)H NMR, (13)C NMR spectral analyses, X-ray diffraction and DTA. The ODBC exhibited the highest degree of oxidation based on the aldehyde group number percentage (82.9%), which confirms the highest reactivity of developed bacterial cellulose [DBC (1)]. The X-ray diffractograms indicated an increase in the interplanar distance of the cellulose Schiff base (6) compared to ODBC (2) due to sulfathiazole (4) inclusion between ODBC (2) sheets corresponding to the 1 1 0 plane. In addition, the aldehyde content of Schiff base (6) was (20.8%) much lower than that of Schiff base (5) (41.5%). These results confirmed the high affinity of sulfathiazole (4) to the ODBC (2) chain, and the substantial changes in the original properties of ODBC were due to these chemical modifications rather than the sulfanilamide (3).