SYNTHESIS OF DIFURAN DIESTERS FROM FURFURAL, AND THEIR EVALUATION AS PLASTICIZERS FOR POLYVINYL-CHLORIDE

The compounds 1,1-bis[5-(2-ethylhexyl, 2-octyl, hexyl, and butyl)carbo xylate-2-furyl)ethane, and 5,5'-dihexylcarboxylate-2,2' bifuran were s ynthesized from furfural and characterized for their plasticizing abil ities toward polyvinyl chloride (PVC) by dynamic mechanical thermal an alyses (DMTA) with di-(2-ethylhexyl) phthalate (DOP) as the standard o f reference. DMTA gave values for the depression of the glass-transiti on temperature (T-g) per mass fraction of plasticizer, and it also yie lded a set of parameters, relative to those of DOP, which describe the compatability of the furan diesters with PVC. These values are compar ed to those of DOP and furan diesters incorporating only one furan rin g in the molecular structure, which have previously been tested by thi s method. The difuran plasticizers are less efficient in lowering T-g than the monofuran plasticizers or DOP, with 1,1-bis[5-(2-octyl)carbox ylate-2-furyl]ethane the least efficient and 1,1-bis(5-hexylcarboxylat e-2-furyl)ethane the most efficient. On average the compatability towa rd PVC is better than that of DOP, and similar to that of analogous mo nofuran structures. (C) 1995 John Wiley and Sons, Inc.