Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Bottino, Francesco A.; Pasquale, Giovanna Di; Pollicino, Antonino

doi:10.1002/(sici)1521-3927(19990801)20:8<405::aid-marc405>3.0.co;2-n

Cited by 18 publications

(5 citation statements)

References 23 publications

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“…4,4‘-Biphenol was purified by crystallization from ethyl alcohol, 4,4‘-sulfonyldiphenol from methyl alcohol/water, and 4,4‘dihydroxybenzophenone from acetone/water; all of the other dihydroxy monomers and diphenyl sulfone (DPS) were crystallized from toluene. Bisfluoro monomer was synthesized as described elsewhere . Other reagents were commercial materials (Aldrich Co).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Characterization, and Study of the Thermal Properties of New Poly(arylene ether 1,3,4-oxadiazole)s

Bottino¹,

Pasquale²,

Iannelli³

2000

Macromolecules

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A series of new poly(arylene ether 1,3,4-oxadiazole)s has been prepared by nucleophilic displacement of aromatic dihalides with aromatic potassium bisphenates in diphenyl sulfone at elevated temperatures. The polymers, characterized by elemental and infrared analysis, GPC, and wide-angle X-ray diffraction, had inherent viscosity from 0.3 to 0.7 dL/g, were obtained in yields higher than 85%, show good solubility in various organic solvents, and had excellent thermal stability as shown by 10% weight loss temperatures in nitrogen and air (above 445 and 440 °C, respectively) and high glass transition temperatures (in the range of 188−226 °C). The introduction of two 1,3,4-oxadiazole units in the polymer repeat unit determines glass transition temperatures higher than those of similar polymers containing only one oxadiazole group in the repeat unit.

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Section: Methodsmentioning

confidence: 99%

“…Bisfluoro monomer was synthesized as described elsewhere. 30 Other reagents were commercial materials (Aldrich Co). All reactions were performed under an inert atmosphere of N2.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Study of the Thermal Properties of New Poly(arylene ether 1,3,4-oxadiazole)s

Bottino¹,

Pasquale²,

Iannelli³

2000

Macromolecules

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“…Other reagent‐grade reagents and solvents were used without purification. 2‐(4‐nitrophenoxy) acetohydrazide was prepared according to the reported method [22]. DGEBA, with epoxy equivalent 185–210, was supplied by Wuxi Resin Works (Wuxi, China).…”

Section: Methodsmentioning

confidence: 99%

“…This is owing to the polymers based on 1,3,4‐Oxadiazoles exhibit good hydrolytic stability, high glass transition temperatures, excellent heat resistance in oxidative atmosphere, low dielectric constants, and tough mechanical properties [19, 21]. Consequently, numerous types of heat‐resistant polymers containing 1,3,4‐oxadiazoles have been synthesized and studied, such as poly(arylene ether)s [22, 23], polyamides [24, 25], and polyimides [26]. It is a meaningful attempt to incorporate 1,3,4‐oxadiazole ring into the BMI skeleton in order to improve some properties thereof without sacrificing mechanical, electrical, thermal performances.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of a novel bismaleimide resin containing 1,3,4‐oxadiazole moiety and the blend systems thereof with epoxy resin

Xiong

Chen

Zhu

et al. 2011

Polymer Engineering & Sci

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A new bismaleimide monomer, 2‐((4‐maleimidophenoxy)methyl)‐5‐(4‐maleimidophenyl)‐1,3,4‐oxadiazole (Mioxd), was designed and synthesized. The chemical structure of the monomer was confirmed by means of Fourier transform infrared (FTIR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy and elemental analysis, and its thermal properties were characterized using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Mioxd as a reactive modifier was blended with epoxy resin based on bisphenol A diglycidyl ether (DGEBA) in weight ratio of 5, 10, and 15%, using 4,4′‐diaminodiphenyl sulfone (DDS) as hardener. The effect of Mioxd addition on the cure behavior and thermal properties of the blend resins was studied by DSC, TGA, and dynamic mechanical analysis (DMA). DSC investigations showed that the main exothermic peak temperature (Tp) of the blend systems did not obviously shift with increasing Mioxd content whereas a new shoulder appeared and gradually grew on the high temperature side of the exothermic peak. The results of DMA measurements exhibited the glassy storage modulus (G') and glass transition temperatures (Tg) increased as the Mioxd content was increased, the cured blends investigated were miscible and no phase separation occurred. Further, the thermal decomposition temperature first decreased and then increased, but the char yield at 600°C increased with an increase in Mioxd content. POLYM. ENG. SCI., 2011. © 2011 Society of Plastics Engineers

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“…Aromatic polyethers are well recognized as a class of high‐performance engineering thermoplastics with the characteristics of good thermooxidative stability, high glass‐transition temperature, and excellent mechanical strength 1–4. The introduction of 1,3,4‐oxadiazole rings into the macromolecular chains of aromatic polyethers improves their properties 5–13. The oxadiazole cycle is similar to a p ‐phenylene structure, which is known to be highly thermoresistant.…”

Section: Introductionmentioning

confidence: 99%

Thermal and electrical properties of copoly(1,3,4‐oxadiazole‐ethers) containing fluorene groups

Hamciuc¹,

Hamciuc²,

Ipate³

et al. 2009

J of Applied Polymer Sci

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A series of aromatic copolyethers containing 1,3,4-oxadiazole rings and fluorene groups was prepared by nucleophilic substitution polymerization technique of 9,9-bis(4-hydroxyphenyl)fluorene, 1, or of different amounts of 1 and an aromatic bisphenol, such as 4,4 0 -isopropylidenediphenol or phenolphthalein, with 2,5-bis(pfluorophenyl)-1,3,4-oxadiazole. The polymers were easily soluble in polar solvents like N-methylpyrrolidone, N,Ndimethylacetamide, N,N-dimethylformamide, and chloroform and can be cast from solutions into thin flexible films. They showed high thermal stability, with decomposition temperature being above 425 C. The polymers exhibited a glass-transition temperature in the range of 195-295 C, with a reasonable interval between glass-transition and decomposition temperature. Electrical insulating properties of some polymer films were evaluated on the basis of dielectric constant and dielectric loss and their variation with frequency and temperature. The values of the dielectric constant at 10 kHz and 20 C were in the range of 3.16-3.25.

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Synthesis and characterization of novel poly(arylene ether)s containing 1,3,4-oxadiazole units

Cited by 18 publications

References 23 publications

Synthesis, Characterization, and Study of the Thermal Properties of New Poly(arylene ether 1,3,4-oxadiazole)s

Synthesis, Characterization, and Study of the Thermal Properties of New Poly(arylene ether 1,3,4-oxadiazole)s

Synthesis and properties of a novel bismaleimide resin containing 1,3,4‐oxadiazole moiety and the blend systems thereof with epoxy resin

Thermal and electrical properties of copoly(1,3,4‐oxadiazole‐ethers) containing fluorene groups

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