Synthesis and characterization of polyesters based on tartaric acid derivatives

• Published in: Polymer (Guilford) Vol. 51; no. 23; pp. 5392 - 5399
• Main Authors: Dhamaniya, Sunil, Jacob, Josemon
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 29.10.2010; Elsevier
• Subjects: Aliphatic polyesters; Applied sciences; Chains (polymeric); Chlorides; Derivatives; Differential scanning calorimetry; Dimethyl; Exact sciences and technology; Hydroxyl functionalized polyesters; l-tartaric acid; Molecular weight; Organic polymers; Physicochemistry of polymers; Polycondensation; Polyester resins; Preparation, kinetics, thermodynamics, mechanism and catalysts; Tartaric acid; Hydroxyl functionalized polyesters; Aliphatic polyesters; l-tartaric acid; Solution polycondensation; Optically active polymer; Ester polymer; Chiral compound; Condensation polymerization; Experimental study; Functional polymer; Thermal stability; Alcohol polymer; Dioxolane derivative polymer; Chemical modification; L-tartaric acid; Aliphatic polymer; Preparation; Optical activity; Deacetalization
• ISSN: 0032-3861; 1873-2291
• DOI: 10.1016/j.polymer.2010.09.034

A series of aliphatic polyesters based on tartaric acid and its derivatives were synthesized starting from naturally occurring L-tartaric acid. The hydroxyl groups of the tartaric acid derivatives were first protected and the polyesters were synthesized by bulk and solution polycondensation methods. Two classes of polyesters were synthesized and characterized, the first by polycondensation of dimethyl 2,3-O-isopropylidene-l-tartrate with various alkanediols, and the second by reaction of 2,3-O-isopropylidene-l-threitol with various diacid chlorides. Acid catalyzed deprotection of isopropylidene groups gave well-defined polyesters having pendant hydroxyl functional groups regularly distributed along the polymer chain. The number average molecular weights (Mn) of the polymers were found to vary in the range of 2.3–15.7 × 103 g mol−1. Differential scanning calorimetry (DSC) analysis showed the glass transition temperatures (Tg) of the polyesters varied from −36.1 °C to 17.9 °C on varying the chain length. [Display omitted]