Synthesis and Characterization of Novel Organosoluble, Thermal Stable and Optically Active Polyesters Derived from 5-(2-Phthalimidiylpropanoylamino)isophthalic Acid

Abstract

ABSTRACT:A new aromatic diacid monomer containing pendent L-alaninephthalimide group was synthesized in three steps in high yield and purity. Several new, highly soluble and optically active aromatic polyesters containing phthalimide and flexible chiral groups were prepared with moderate molecular weights by direct polycondensation with tosyl chloride (TsCl), pyridine (Py) and N,N-dimethylformamide (DMF) as condensing agent. The aim of this work was to obtain novel optically active polyesters that were more soluble in common organic solvents while maintaining the high thermal stability. All polymers derived from such a diacid and aromatic diols were highly organosoluble in the solvents like N-methyl-2-pyrrolidinone, N,N-dimethylacetamide, DMF, Py and dimethyl sulfoxide. These new optically active polyesters with inherent viscosities ranging from 0.21 to 0.81 dL/g were obtained with high yields. Thermogravimetric analysis (TGA) data showed that these polyesters are thermal stable, with 10% weight loss being recorded above 370 C. Some of the above polymers were characterized by 1 H-NMR, FT-IR, elemental analyses and specific rotation techniques. [doi:10.1295/polymj.PJ2007061] KEY WORDS Polyester / Optically Active Polymers / TsCl/Py/DMF Condensing Agent / Thermal Properties / Solubility / Direct Polycondensation / Polyesters (PE)s are significant class of high performance and engineering macromolecules, which find utilize in a number of various applications.

Preparation and characterization of new thermally stable and optically active polyesters by direct polycondensation reaction promoted by Vilsmeier adduct

“…T 10 (°C), char Yield and LOI of these polymers are in the range of 400-420, 9-19, 20-25, respectively. The obtained results showed that spacer containing polymers enjoyed higher thermal stabilities in comparison with no spacer ones [27].The T g s of the PEs were determined by DSC and the results are given in Table 3. The DSC analyses for PEs show T g around 200-240 °C .…”

Advances in synthetic optically active condensation polymers - A review

“…Recently, Mallakpour and coworkers [127][128][129][130][131] synthesized optically active thermally stable aromatic polyesters (PE)s containing phthalimide group from the reaction of two different diacid monomer with several aromatic diols via direct polyesterification with tosyl chloride (TsCl)/Py/ Figure 10. Synthesis of optically active coPIs derived from DAn [119][120][121][122][123] DMF system as condensing agent.…”

Kinetics and Thermal Degradation Study of Optically Active and Thermally Stable Aromatic Polyamides with Flame-Retardancy Properties

“…By comparison of the results with the values obtained by Criado method we found the mechanism which best describes the thermal decomposition of PAs corresponding to the mechanism F1 (Random nucleation with one nucleus on the individual particle). The Z() master curves can be plotted using eq (17) 385 453 48 197 68 PA6 422 449 52 225 70 PA10 378 409 48 212 65 PA11 436 495 58 236 67 a Temperature at which 5% weight loss was recorded by TGA at a heating rate of 10 C/min. in a nitrogen atmosphere.…”

“…The incorporation of pendent bulky, packing-disruptive groups along the polymer backbone outcomes in a less ordered polymer matrix, hence increasing the solubility characteristics, while other advantageous properties are retained. [16][17][18][19] The improvement of the fire behavior and thermal stability of polymer is today the aim of numerous studies. The research and development of flame retardant polymeric materials always receives great attention whether in fundamental research or industry exploitation.…”