New organosoluble polyarylates containing pendent fluorene units: synthesis, characterization and thermal behaviour

Abstract

The new pendent bisphenol containing flourene unit, 1,1-bis-[(4-hydroxyphenyl)-1-(9H-fluoren-2-yl)]ethane (BHPFE) are synthesized from commercially available 2-acetylfluorene and phenol and then utilized for the synthesis of three new kinds of polyarylates by phase-transfer catalyzed interfacial polycondensation technique with two different benzenedicarbonyl chlorides (isophthaloyl chloride (IPC) and terephthaloyl chloride (TPC)) and its mixture of 50:50 mol%. The synthesized BHPFE and polyarylates are well-characterized using FTIR, 1H-NMR, 13C-NMR, and GPC measurements. Results of these new polyarylates are compared with aromatic polyesters derived from Bisphenol-A with TPC as well as IPC. Inherent viscosities and number average molecular weights (Mn) of polyarylates are found in the range of 0.11–0.71 dl/g and 59,516–79,371 g/mol, respectively. Compared with the polyarylates synthesized from Bisphenol-A, the polyarylates synthesized from BHPFE monomers exhibited high solubility in various organic solvents like dichloromethane, tetrahydrofuran, chloroform, pyridine and N, N-dimethylformamide and could be easily solution-cast into transparent films. The WXRD study indicated that new polyarylates are amorphous in nature. Polyarylates showed the glass transition temperature (Tg) inbetween 123–151 °C and 10% weight loss (T10) ranging from 399°–447 °C under nitrogen atmosphere indicating their thermal stability. Polyarylates having tensile strength of 3.35 to 5.36 MPa with optical transparency cutoff in the wavelength of 309–326 nm range.