Polymerization of l-lactide with SnCl2: A Low Toxic and Eco-friendly Catalyst

Polymerizations of l-lactide catalyzed either by neat SnCl₂ or by SnCl₂?+?difunctional cocatalysts were conducted in bulk at 180, 160 and 140 °C with variation of the Lac/Cat ratio and time. With neat SnCl₂ poly(L-lactide) having weight average molecular weights (uncorrected M_w’s) up to 190 000 g mol^?1 were obtained mainly consisting of linear chains. Addition of salicylic acid or 1,1-bisphenol yielded a higher fraction of cyclic polylactides but lower molecular weights. Furthermore, SnCl₂ was compared with Bu₂SnCl₂ and various other metal chlorides and the best results were obtained with SnCl₂. With ethyl L-lactate as initiator SnCl₂-catalyzed ROPs were performed at 120 °C and the lac/initiator ratio was varied. All these experiments were conducted under conditions allowing for comparison with ROPs catalyzed with neat Sn(II)-2-ethyhexanoate. Such a comparison was also performed with ε-caprolactone as monomer.

     

Syntheses and application of polylactides

Polylactides can be prepared by direct polycondensation of lactic acid, or better, by ring-opening polymerization of cyclic dilactides (usually called lactides). These lactides exist in the form of four stereoisomers two of which (L,L- and rac. -D,L-) are technically produced in large quantities. These lactides can by polymerized via four different classes of initiators and reaction mechanisms. The characteristics mechanistic and preparative features of the cationic polymerization, anionic polymerization and of the coordination-insertion mechanism are described. Furthermore, copolymerizations of lactides with glycolide or epsilon-caprolactone and their analytical problems are discussed. Finally, a new type of wound dressing based on transparent are resorbable films of copolylactides is mentioned.