Synthesis and MALDI-TOF MS Characterization of High Molecular Weight Poly(1,2-dihydroxybenzenephthalates) Obtained by Uncatalyzed Bulk Polymerization of O,O’-phthalyd-3-ylidene catechol or 4-Methyl-O,O'-phthalyd-3-ylidenecatechol

A new procedure to obtain high molecular weight poly(1,2-dihydroxybenzene phthalates)by bulk polymerization of some spiro-compounds is described. O,O′-Phthalid-3-ylidenecatechol (I) and4-methyl-O,O′-phthalid-3-ylidenecatechol (II) spiro-compounds have been synthesized and used asmonomers. Poly(1,2-dihydroxybenzene phthalate) (III) and poly(1,2-dihydroxy-4-methylbenzene phtha-late) (IV) have been prepared by heating at 200 °C of spiro-compounds IandII, respectively, withoutaddition of catalyst. The resulting polyestersIIIandIVhave been characterized by GPC, TG, DSC,NMR, FAB-MS, and MALDI-TOF MS analyses. The GPC curves of the obtained materials showed thathigh molecular weight polyesters, containing only a very little amount of low molecular weight oligomers,have been formed. The structural characterization of these polyesters by FAB and MALDI-TOF massspectrometric analyses showed that they are constituted exclusively of open-chain macromolecules havingboth hydroxy end-groups. Data collected suggest that in the bulk polymerization of spiro-compoundsIandIIa possible chain growth mechanism of polymerization is active, which is strongly inhibited by acidspecies.