SYNTHESIS AND CHARACTERIZATION OF NEW THERMALLY STABLE POLYAMIDES BASED ON 2, 5-PYRIDINE DICARBOXYLIC ACID AND HYDANTOIN DERIVATIVES

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FAGHIHI KH.

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Journal: JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY) Year:2011 | Volume:21 | Issue:80 (CHEMISTRY ISSUE) Page(s): 85-92

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Title

SYNTHESIS AND CHARACTERIZATION OF NEW THERMALLY STABLE POLYAMIDES BASED ON 2, 5-PYRIDINE DICARBOXYLIC ACID AND HYDANTOIN DERIVATIVES

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FAGHIHI KH. | Issue Writer Certificate

Keywords

POLYAMIDESQ2

PYRIDYL MOIETYQ2

HYDANTOIN DERIVATIVESQ3

DIRECT POLYCONDENSATIONQ2

Abstract

Introduction: Aromatic POLYAMIDES have received considerable attention with regard to the production of high performance materials due to their outstanding thermal stability, chemical resistance and electrical and mechanical properties. However their application are restricted because of their poor solubility in organic solvents and too high glass transition temperatures that make them very difficult to be processed by spin coating or thermoforming techniques. Much effort has been made to create structurally modified aromatic polymers having increased solubility and processability with retention of their high thermal stability. It is known that the solubility of polymers is often increased when flexible bonds such as [-O-, -SO2-, -CH2-, -C (CF3-)2], bulky pendent groups (such as t-butyl, adamantyle and naphtyl), large pendent groups or polar constituents such as heterocyclic segments are incorporated into the polymer backbone due to the altering crystallinity and intermolecular interactions.Aim: In this article, synthesis and characterization of six new POLYAMIDES 3a-fcontaining pyridyl and hydantoin moieties in the main chain from the polycondensation reaction of 2, 5-pyridine dicarboxylic acid 1 with six different of hydantoins derivatives 2a-f such as hydantoin 2a, 5, 5-dimethyl hydantoin 2b, 5-ethyl, 5-methyl hydantoin 2c, 5, 5-diethyl hydantoin 2d, 5, 5-spirocyclopantyl hydantoin 2e, spirocyclohyxyl hydantoin 2f by using Nmethyl- 2-pyrrolidone (NMP), triphenylphosphite and pyridine as condensing agents was reported.Materials and Methods: All chemicals were purchased from Fluka and Merck Chemical Company. The 1H-NMR spectrum (300 MHz) was recorded on a Bruker Avance 300 spectrometer (Germany). Fourier transform infrared (FT-IR) spectra were recorded on a Galaxy series FTIR 5000 spectrophotometer (England).Results: Six new thermally stable POLYAMIDES 3a-f were synthesized through the polycondensation reaction of 2, 5-pyridine dicarboxylic acid 1 with six different derivatives of hydantoins 2a-f in a medium consisting of N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride and pyridine. The polycondensation reaction produced a series of novel POLYAMIDES containing pyridyl and hydantoin moieties in the main chain in high yield with inherent viscosities between 0.56-0.80 dL/g. The resulting polymers were fully characterized by means of FT-IR spectroscopy, elemental analyses, inherent viscosity, and solubility tests. Thermal properties of these polymers were investigated by using thermal gravimetric analysis (TGA), differantional thermal gravimetric (DTG). Conclusion: This work involved the syntheses of several new PAs 3a-f through the DIRECT POLYCONDENSATION reaction of diacid 1 with six hydantoin compounds 2a-f by using triphenyl phosphite, NMP, calcium chloride and pyridine as condensing agents. These new PAs were soluble in various organic solvents and had good thermal stability. The presence of pridyl segments as a hetrocyclic ring into the backbone increased the solubility of these polymers. These properties could make these PAs attractive for practical applications, such as processable high-performance engineering plastics.

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APA: Copy

FAGHIHI, KH.. (2011). SYNTHESIS AND CHARACTERIZATION OF NEW THERMALLY STABLE POLYAMIDES BASED ON 2, 5-PYRIDINE DICARBOXYLIC ACID AND HYDANTOIN DERIVATIVES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), 21(80 (CHEMISTRY ISSUE)), 85-92. SID. https://sid.ir/paper/70576/en

Vancouver: Copy

FAGHIHI KH.. SYNTHESIS AND CHARACTERIZATION OF NEW THERMALLY STABLE POLYAMIDES BASED ON 2, 5-PYRIDINE DICARBOXYLIC ACID AND HYDANTOIN DERIVATIVES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY)[Internet]. 2011;21(80 (CHEMISTRY ISSUE)):85-92. Available from: https://sid.ir/paper/70576/en

IEEE: Copy

KH. FAGHIHI, “SYNTHESIS AND CHARACTERIZATION OF NEW THERMALLY STABLE POLYAMIDES BASED ON 2, 5-PYRIDINE DICARBOXYLIC ACID AND HYDANTOIN DERIVATIVES,” JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), vol. 21, no. 80 (CHEMISTRY ISSUE), pp. 85–92, 2011, [Online]. Available: https://sid.ir/paper/70576/en

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