Synthesis and Properties of Novel Cardo Aromatic Poly(ether oxadiazole)s and Poly(ether-amide oxadiazole)s

Hsiao, Sheng‐Huei; He, Ming-Hsiang

doi:10.1002/1521-3935(20011201)202:18<3579::aid-macp3579>3.3.co;2-f

Cited by 8 publications

(8 citation statements)

References 2 publications

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“…The bis(ether‐acyl chloride) monomers, 1,1‐bis[4‐(4‐chloroformylphenoxy)phenyl]cyclohexane ( 1a ) (mp 86–87 °C), 5,5‐bis[4‐(4‐chloroformylphenoxy)phenyl]‐4,7‐methanohexahydroindan ( 1b ) (mp 70–72 °C), and 9,9‐bis[4‐(4‐chloroformylphenoxy)phenyl]fluorene ( 1c ) (mp 256–258 °C), were prepared by chlorinating the corresponding bis(ether‐carboxylic acid)s16–18 with thionyl chloride in the presence of one drop of N , N ‐dimethylformamide (DMF) as a catalyst. Details of the synthesis and characterization data of these diacyl chlorides have been described in a separate article 20. The aromatic bis( o ‐aminophenol) monomers including 4,4′‐diamino‐3,3′‐dihydroxybiphenyl ( 2 ) [Tokyo Chemical Industry (TCI) Japan], 3,3′‐diamino‐4,4′‐dihydroxybiphenyl ( 3 ) (TCI), and 2,2‐bis(3‐amino‐4‐hydroxyphenyl)hexafluoropropane ( 4 ) (TCI) were of high purity and used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of novel cardo aromatic poly(ether‐benzoxazole)s

Hsiao

2001

J. Polym. Sci. A Polym. Chem.

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Three new bis(ether-acyl chloride) monomers, 1,1-bis[4-(4-chloroformylphenoxy)phenyl]cyclohexane (1a), 5,5-bis[4-(4-chloroformylphenoxy)phenyl]-4,7-methanohexahydroindan (1b), and 9,9-bis[4-(4-chloroformylphenoxy)phenyl]fluorene (1c), were synthesized from readily available compounds. Aromatic polybenzoxazoles bearing ether and cardo groups were obtained by the low-temperature solution polycondensation of the bis(ether-acyl chloride)s with three bis(aminophenol)s and the subsequent thermal cyclodehydration of the resultant poly(o-hydroxy amide)s. The intermediate poly(o-hydroxy amide)s exhibited inherent viscosities in the range of 0.35-0.71 dL/g. All of the poly(o-hydroxy amide)s were amorphous and soluble in many organic polar solvents, and most of them could afford flexible and tough films by solvent casting. The poly(o-hydroxy amide)s exhibited glass-transition temperatures (T g 's) in the range of 141-169°C and could be thermally converted into the corresponding polybenzoxazoles approximately in the region of 240 -350°C, as indicated by the DSC thermograms.Flexible and tough films of polybenzoxazoles could be obtained by thermal cyclodehydration of the poly(o-hydroxy amide) films. All the polybenzoxazoles were amorphous and showed an enhanced T g but a dramatically decreased solubility as compared with their poly(o-hydroxy amide) precursors. They exhibited T g 's of 215-272°C by DSC and showed insignificant weight loss before 500°C in nitrogen or air.

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Section: Methodsmentioning

confidence: 99%

Synthesis and properties of novel cardo aromatic poly(ether‐benzoxazole)s

Hsiao

2001

J. Polym. Sci. A Polym. Chem.

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“…Compared with conventional polymers, cardo polymers possess better thermal stability (high T g ) and mechanical properties as well as solubility in polar solvents, which are important for rigid aromatic polymers. Many polymers with cardo groups have been synthesized, including polyarylates,2–4 polycarbonates,5, 6 polyimides,7–9 polyamides,8, 10 poly(arylene ether sulfone)s (PESs),11–26 poly(arylene ether ketone)s,11, 27 and poly ether oxadiazoles,28 among others. Of these, cardo PES is of great interest since this is one of the most popular families of high performance engineering thermoplastics.…”

Section: Introductionmentioning

confidence: 99%

Phenolphthalein‐based cardo poly(arylene ether sulfone): Preparation and application to separation membranes

Gao

Zhang

2012

J of Applied Polymer Sci

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Cardo poly(arylene ether sulfone)s are an important type of high performance engineering thermoplastics. They possess unique properties, including good processability, thermal stability, and good insulating and mechanical properties as well as excellent chemical resistance. They are potential candidates for the preparation of ion exchange, water purification, and gas separation membranes. This review focuses on the synthesis of phenolphthalein-based cardo poly(arylene ether sulfone)s, including synthesis of cardo bisphenols and their polymers, and their application to separation membranes.

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“…Much effort has been made to improve the mechanical and physical properties of polyaspartimides, e.g. to find new solutions systems and to modify their structures by introducing bulky substituents, incorporation of flexible linkages into the backbone, or by copolymerization [18,19].…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of bismaleimide monomers with various structures

Sava¹

2012

Designed Monomers and Polymers

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A series of bismaleimide monomers (BMI) with various structures containing flexible linkages was prepared and structural characterization of these compounds was carried out by elemental analysis, Fourier transform infrared spectroscopy, and 1 HÀNMR spectroscopy. The thermal behavior of these monomers (BMI(1-4)) was investigated by differential scanning calorimetry, polarized light microscopy and thermogravimetric analysis. The reactivity of the bismaleimide compounds is influenced by chemical nature of the bridge unit between the maleimide rings. The monomers were soluble in several organic solvents, the 10% weight loss temperatures were above 500°C, and char yield at 700°C ranged between 46 and 58% in nitrogen atmosphere. Birefringence in melting state was observed for two bismaleimides (BMI-3 and BMI-4) which could indicate a possible thermotropic liquid crystalline behavior.

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Synthesis and Properties of Novel Cardo Aromatic Poly(ether oxadiazole)s and Poly(ether-amide oxadiazole)s

Cited by 8 publications

References 2 publications

Synthesis and properties of novel cardo aromatic poly(ether‐benzoxazole)s

Synthesis and properties of novel cardo aromatic poly(ether‐benzoxazole)s

Phenolphthalein‐based cardo poly(arylene ether sulfone): Preparation and application to separation membranes

Preparation and characterization of bismaleimide monomers with various structures

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