Biobased Plasticizers from Tartaric Acid: Synthesis and Effect of Alkyl Chain Length on the Properties of Poly(vinyl chloride)

A series of tartaric acid (TA) esters with different side chain lengths [dibutyl TA esters (DBTAE)-Cn], as plasticizers for poly(vinyl chloride) (PVC), is herein reported. Their structures have been fully characterized using proton nuclear magnetic resonance and Fourier-transform infrared spectroscopy. Their compatibility and plasticizing effect for soft PVC were evaluated using thermogravimetric analysis, dynamic mechanical analysis, tensile testing, and migration testing. The results showed that all these TA esters exhibit good plasticizing performance. At a concentration of 30 phr in PVC, the best results for the plasticizing effect, in terms of glass transition temperature reduction and elongation at break, were achieved when the ester DBTAE-C4 was used. However, the longer side chains of these esters improved the thermal stability of soft PVC blends yet exacerbated the migration behavior of these esters from PVC films in n-hexane. The properties of the plasticized PVC blends depended on the structural features of DBTAE-Cn. The plasticizing performances of the esters DBTAE-C1 and DBTAE-C4 rivaled that of dioctyl phthalate (DOP), suggesting that they have the potential to replace DOP in soft PVC materials.