Synthesis and properties of novel aromatic poly(o-hydroxy amide)s and polybenzoxazoles based on the bis(ether benzoyl chloride)s from hydroquinone and its methyl-,tert-butyl-, and phenyl-substituted derivatives

Hsiao, Sheng‐Huei; Dai, Liang-Ru

doi:10.1002/(sici)1099-0518(19990701)37:13<2129::aid-pola28>3.0.co;2-o

Cited by 27 publications

(15 citation statements)

References 18 publications

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“…The appearance of new absorption band at 1624 cm −1 (-C=N str.) [17][18][19][20]22 proves the formation of PBO 3. Obtained 3 were insoluble in NMP.…”

Section: Resultsmentioning

confidence: 95%

“…After heating at 450 • C, all films became brittle. FT-IR spectra showed small changes of the absorption bands after heating at 450 • C in comparison with polymers before 13,14 ) appeared after heating at 400 • C. The results of IR investigation indicated that functionalized PIOHs were not converted to PBOs by heating up to 450 • C As it was found that thermal conversion from PIOHs 2 to PBOs 3 seemed to be difficult because of rigid structure of DAR, preparation of PBO by thermal conversion of poly(o-hydroxyamide)s (PAOHs) [16][17][18][19][20][21][22] that were prepared from DAR was investigated as comparison. Such rearrangement to PBOs has been described to occur at lower temperatures.…”

Section: Resultsmentioning

confidence: 99%

“…There have been many reports for PBOs preparation via the PAOHs precursor method, 5,[16][17][18][19][20][21][22][23] whereas not so many papers describe about the thermal conversion of PIOHs to PBOs. After the first synthesis of poly(3,3 -dihydroxy 4,4 -diphenylene) pyromellitimide and thermal conversion to the corresponding PBO was reported by Kardash et al in 1967, 24 several studies have been reported.…”

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confidence: 99%

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Thermal Rearrangement of Poly(o-hydroxyimide)s Synthesized from 4,6-Diaminoresorcinol Dihydrochloride

Schab‐Balcerzak

Jikei

Kakimoto

2003

Polym J

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KEY WORDSPoly(o-hydroxyimide)s / Poly(o-hydroxyamide)s / Polybenzoxazoles / 4,6-Diaminoresorcinol Dihydrochloride / Aromatic polybenzoxazoles (PBOs) are well known as high performance polymeric materials due to their excellent thermal stability, high solvent and chemical resistance, thermo-oxidative stability and outstanding mechanical properties, which make them attractive for many applications such as fabrication of high-strength and high-modulus fibers. [1][2][3][4] PBOs have been prepared by several methods, i.e., a one-step solution polycondensation of bis(oaminophenol)s with aromatic dicarboxylic acids in polyphosphoric acid, a melt polycondensation of bis(oaminophenol)s with diacid diphenyl esters. 8 Alternatively, they have been synthesized by two-step methods starting from bis(o-aminophenol)s or their trimethylsilylated derivatives [5][6][7]9 with aromatic dicarboxylic acid chlorides or tetracarboxylic anhydrides giving precursor poly(o-hydroxyamide)s (PAOHs) or poly(ohydroxyimide)s (PIOHs) followed by thermal rearrangement of the hydroxy-containing precursors to the final PBOs. Using the precursor polymers has advantage in processability of precursors even though almost PBOs do not dissolve in organic solvents, and do not melt at elevated temperatures.There have been many reports for PBOs preparation via the PAOHs precursor method, 5, 16-23 whereas not so many papers describe about the thermal conversion of PIOHs to PBOs. After the first synthesis of poly(3,3 -dihydroxy 4,4 -diphenylene) pyromellitimide and thermal conversion to the corresponding PBO was reported by Kardash et al. in 1967, 24 several studies have been reported. [10][11][12][13][14][15] Although PIOHs has been prepared from the smallest diamino-diphenol monomer, 4,6-diaminoresorcinol, 25 it is noteworthy that no report was found concerning the thermal rearrangement of PIOHs synthesized from 4,6-diaminoresorcinol to PBOs that are expected to possess high modulus and high strength because of their compact rigid rod structure.In this paper, we describe results in synthesis of PIOHs from 4,6-diaminoresorcinol dihydrochloride (DAR), and attempts of thermal conversion to PBOs. Preparation of PBOs via the PAOHs rout is also described in comparison. EXPERIMENTAL MaterialsAromatic tetracarboxylic acid dianhydrides 1: pyromellitic dianhydride (PMDA) 1a, 3, 3 , 4, 4 -biphenyl tetracarboxylic dianhydride (BPDA) 1b, 3, 3 , 4, 4 -oxydiphthalic anhydride (ODPA) 1c, and 3, 3 , 4, 4 -benzophenonetetracarboxylic dianhydride (BTDA) 1d were sublimated prior to use. 4,6-Diaminoresorcinol dihydrochloride (DAR) was recrystallized from water with HCl and dried at 80 • C in vacuum. 3, 3 -Dihydroxy-4, 4 -aminobiphenyl (HAB) was recrystallized from a water/DMAc cosolvent and dried at 60 • C in vacuum. 12 Isophthalic acid 6a, terephthalic acid 6b, 4, 4 -dicarboxydiphenyl ether 6c, and 4, 4 -biphenyldicarboxylic acid 6d were used as received. N-Methyl-2-pyrrolidinone (NMP) was stirred over calcium hydride overnight and then distilled under reduced pressure. Measur...

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“…The appearance of new absorption band at 1624 cm −1 (-C=N str.) [17][18][19][20]22 proves the formation of PBO 3. Obtained 3 were insoluble in NMP.…”

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Thermal Rearrangement of Poly(o-hydroxyimide)s Synthesized from 4,6-Diaminoresorcinol Dihydrochloride

Schab‐Balcerzak

Jikei

Kakimoto

2003

Polym J

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“…Many studies have been performed by replacing the hydroxyl groups with halogen-based substituents on the benzene ring of PHAs. Various attempts have also been made to improve the solubility and reduce the thermal cyclization temperature by introducing flexible or bulky groups into the main-chain of PHA [9][10][11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal properties of polyhydroxyamide copolymer and its derivatives

et al. 2016

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We synthesized a polyhydroxyamide (PHA) copolymer via low-temperature solution polymerization of 3,3'-dihydroxybenzidine with terephthaloyl chloride (80.0 mol%) and isophthaloyl chloride (20.0 mol%) in N,Ndimethylacetamide with the aid of LiCl. We prepared the PHA copolymer derivatives containing the fluorine-based substituents and investigated their solubility, cyclization behavior, and thermal properties using a differential scanning calorimeter (DSC), a thermogravimetric analyzer (TGA), and the simultaneous thermogravimetric analyzer coupled with a mass spectrometer (STA-MS). The chemical structures of the PHA copolymer and its derivatives, as well as the polybenzoxazoles (PBOs) obtained through thermal cyclization of the copolymer and derivatives, were determined by a fourier transform infrared (FT-IR) spectroscopic analysis. The PHA copolymer could be dissolved in organic solvents only with the aid of LiCl, while its derivatives were readily soluble in DMA c and NMP without LiCl at room temperature. The DSC and TGA results demonstrated that the PHA copolymer derivatives could be converted to PBOs at a lower temperature than the PHA copolymer.

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“…But the rigid-rod nature of polybenzazoles polymer chain makes them quite insoluble in organic solvents and difficult to process [6]. Several ways have been performed to improve the solubility and photoluminescence properties of polybenzazoles, such as introducing a big substitute group into the side chain [7][8][9] and soft segments into main chain [10][11][12]. Jenekhe and co-workers have synthesized rod-coil copolymers consisting of electro-active and photoactive segments [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of polybenzazoles containing flexible methylene in backbone

Liu

Zhuang

et al. 2008

Front. Chem. Eng. China

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A novel series of polybenzazoles with rigid-rod benzoxazole cycle and soft methylene segment was designed and synthesized via solution condensation polymerizations from 4,6-diamino-1,3-benzenediol diphosphate, terephthalic acid and aliphatic dicarboxylic acid. The structures of polybenzazoles were characterized by means of FT-IR, 1 H NMR and Wide-angle X-ray diffraction (WAXRD). All the polymers show excellent thermal stability and the T d s was above 471uC. The intrinsic viscosities [g] of the polymers ranged from 0.8 to 0.9. The UV-Vis absorption peaks of the polymers in MSA were blue-shifted from 429 nm for PBO to 291 nm for PBOC7, and the Stokes shifts in PL spectra enlarged.

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Synthesis and properties of novel aromatic poly(o-hydroxy amide)s and polybenzoxazoles based on the bis(ether benzoyl chloride)s from hydroquinone and its methyl-,tert-butyl-, and phenyl-substituted derivatives

Cited by 27 publications

References 18 publications

Thermal Rearrangement of Poly(o-hydroxyimide)s Synthesized from 4,6-Diaminoresorcinol Dihydrochloride

Thermal Rearrangement of Poly(o-hydroxyimide)s Synthesized from 4,6-Diaminoresorcinol Dihydrochloride

Synthesis and thermal properties of polyhydroxyamide copolymer and its derivatives

Synthesis and properties of polybenzazoles containing flexible methylene in backbone

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