SYNTHESIS AND MALDI-TOF MS CHARACTERIZATION OF HIGH-MOLECULAR-WEIGHT POLY(1,2-DIHYDROXYBENZENE PHTHALATES) OBTAINED BY UNCATALYZED BULK-POLYMERIZATION OF O,O'-PHTHALID-3-YLIDENECATECHOL OR 4-METHYL-O,O'-PHTHALID-3-YLIDENECATECHOL

A new procedure to obtain high molecular weight poly(1,2-dihydroxybenz ene phthalates) by bulk polymerization of some spiro-compounds is desc ribed. O,O'-Phthalid-3-ylidenecatechol (I) and 4-methyl-O,O'-phthalid- 3-ylidenecatechol (II) spiro-compounds have been synthesized and used as monomers. Poly(1,2-dihydroxybenzene phthalate) (III) and poly(1,2-d ihydroxy-4-methylbenzene phthalate) (IV) have been prepared by heating at 200 degrees C of spiro-compounds I and II, respectively, without a ddition of catalyst. The resulting polyesters III and TV have been cha racterized by GPC, TG, DSC, NMR, FAB-MS, and MALDI-TOF MS analyses. Th e GPC curves of the obtained materials showed that high molecular weig ht polyesters, containing only a very little amount of low molecular w eight oligomers, have been formed. The structural characterization of these polyesters by FAB and MALDI-TOF mass spectrometric analyses show ed that they are constituted exclusively of open-chain macromolecules having both hydroxy end-groups. Data collected suggest that in the bul k polymerization of spiro-compounds I and II a possible chain growth m echanism of polymerization is active, which is strongly inhibited by a cid species.