NEW POLYESTERS DERIVED FROM 4-PHENYLENEDIACRYLIC ACID AND AROMATIC DIOLS: SYNTHESIS AND PROPERTIES

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FAGHIHI K.

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Journal: JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY) Year:2009 | Volume:19 | Issue:72 (CHEMISTRY ISSUE) Page(s): 69-76

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Title

NEW POLYESTERS DERIVED FROM 4-PHENYLENEDIACRYLIC ACID AND AROMATIC DIOLS: SYNTHESIS AND PROPERTIES

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FAGHIHI K. | Issue Writer Certificate

Keywords

POLYESTERSQ3

4-PHENYLENEDIACRYLIC ACIDQ3

AROMATIC DIOLQ3

Abstract

Introduction: Aromatic POLYESTERS are certainly one of the most successful classes of high-temperature polymers. However these polymers encounter processing difficulty due to their infusibility and poor solubility in organic solvents. Therefore, more researches have been focused on maintaining considerable thermally stable and improving their solubility. These studies include: 1) Introducing rather soft segments on the main chain such as methylene and vinyl segments 2) Breaking its symmetry and regularity, thereby making crystallization impossible 3) Introducing the bulky side groups to be exempt from crystallization and 4) Destroying the hydrogen bonding by N-substitution with certain groups such as methyl.Aim: In this paper a series of novel POLYESTERS were obtained by the solution polycondensation reaction of p-phenylene diacryloyl chloride (4) with six different of AROMATIC DIOLs (5a-f) in DMAc solvent and in the presence of pyridine as a base. These polymers have a soft segment such as vinyl moiety in the main chain for improving the solubility in organic solvents in compare to aromatic POLYESTERS. These polymers have been noticed because they can be used for preparing photosensitive liquid crystalline polymers. There are some reported papers about synthesis polyamides, polyimides, POLYESTERS and poly (amid-co-imide) s containing p-phenylenediacrylic moiety in the main chain.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: p-Phenylenediacrylic acid (3) was prepared by the reaction of terephthal aldehyde (1) and malonic acid (2) in the presence of pyridine. The diacid (3) was then converted to p-phenylenediacryloyl chloride (4) by the reaction with thionyl chloride. Solution polycondensation reactions of diacid chloride (4) with hydroquinone (5a), 2, 7- dihydroxy naphtalene (5b), 4, 4΄-dihydroxy diphenyl sulfone (5c), bisphenol A (5d), 1, 4- dihydroxy antraquinone (5e) and phenol phethalein (5f) were carried out in DMAc solution and in the presence of pyridine as a base. The polycondensation reactions produce a series of new POLYESTERS (6a-f) in high yields having inherent viscosity between 0.32-0.50 dL/g. The resulting POLYESTERS were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), differential scanning calorimetry (DSC), solubility test and FT-IR spectroscopy.Conclusion: Several new POLYESTERS (6a-f) have been synthesized by the solution polycondensation reaction of the monomer (4) with six different of AROMATIC DIOLs (5a-f) in DMAc in the presence of pyridine as a base. These new POLYESTERS are soluble in various organic solvents and have good thermal stability. These properties can make these POLYESTERS attractive for practical applications such as processable high-performance engineering plastics.

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APA: Copy

FAGHIHI, K.. (2009). NEW POLYESTERS DERIVED FROM 4-PHENYLENEDIACRYLIC ACID AND AROMATIC DIOLS: SYNTHESIS AND PROPERTIES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), 19(72 (CHEMISTRY ISSUE)), 69-76. SID. https://sid.ir/paper/70612/en

Vancouver: Copy

FAGHIHI K.. NEW POLYESTERS DERIVED FROM 4-PHENYLENEDIACRYLIC ACID AND AROMATIC DIOLS: SYNTHESIS AND PROPERTIES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY)[Internet]. 2009;19(72 (CHEMISTRY ISSUE)):69-76. Available from: https://sid.ir/paper/70612/en

IEEE: Copy

K. FAGHIHI, “NEW POLYESTERS DERIVED FROM 4-PHENYLENEDIACRYLIC ACID AND AROMATIC DIOLS: SYNTHESIS AND PROPERTIES,” JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), vol. 19, no. 72 (CHEMISTRY ISSUE), pp. 69–76, 2009, [Online]. Available: https://sid.ir/paper/70612/en

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