Direct synthesis of poly(phenyl ester)s by using triphenyl‐phosphine and carbon tetrachloride as condensing agents

Higashi, Fukuji; Murakami, Tomoyoshi

doi:10.1002/marc.1981.030020405

Cited by 14 publications

(4 citation statements)

References 6 publications

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“…The short methyl moiety of PABA 1 could distort the crystal lattice to afford a packing structure that is different from the others. In addition, the periodicity of 10.8 Å observed in the case of PABA 1 and 13.0 Å in the case of PABA n ( n = 3, 4, and 5) could be attributed to the pitch of the helix formed due to the structural propensities of the cis conformation of N-alkylated amide bonds and syn arrangement of the benzene ring . Several researchers have studied the crystalline structure of PABA 0 (polybenzamide) with no alkyl side chains, where the polymers are tightly packed to form orthorhombic systems due to the hydrogen bonding of amide groups (trans conformation) (order parameters of a = 7.74, b = 5.27, and c = 12.82 Å) .…”

Section: Resultsmentioning

confidence: 99%

Surface Morphological Changes in Monolayers of Aromatic Polyamides Containing Various N-Alkyl Side Chains

Fujimori

Chiba²,

Sato³

et al. 2010

J. Phys. Chem. B

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We synthesized new aromatic polyamides (poly-(N-alkylated benzamides), abbrev. PABA(n)) having both a rigid main chain and a flexible side chain with different lengths. We investigated the solid-state structures, that is, the molecular orientation and surface morphology, of organized molecular films of PABA(n) by performing surface pressure-area (pi-A) isotherm, in-plane and out-of plane X-ray diffraction (XRD), polarized infrared spectroscopy, and atomic force microscopy (AFM) measurements. The solid-state structure of poly-(N-methyl benzamide) (PABA(1)) belonged to the monoclinic system, whereas PABA(3), PABA(4), and PABA(5) showed an orthorhombic packing pattern. PABA(7) and PABA(8) formed amorphous polymers. In the case of PABA(17), a two-dimensional hexagonal lattice was formed as a subcell consisting of side chains. These polymer monolayers were highly condensed on a water surface at 15 degrees C. Out-of-plane XRD measurement results showed that the PABA(1), PABA(3), PABA(4), and PABA(5) multilayers showed large periodicities of 50-60 A. From AFM observation results, it was found that these aromatic polyamides formed single particle layers of hydrophilic groups localized at the bottom of the particles. On the other hand, PABA(7) and PABA(8) monolayers showed irregularity and exhibited shapeless morphologies. In addition, an organized molecular film of PABA(17) formed a highly ordered layer structure (periodicity of 30 A) and a giant circular domain (diameter of 20 nm) made of a side chain crystal. The PABA(17) monolayer showed a hexagonal packing pattern formed due to van der Waals interaction between the flexible side chains. From these experimental findings, it was concluded that the polymer synthesis method employed in the present study can be directly used to control the crystal structure (the third order structure of polymers), molecular arrangement, and surface morphologies of polymer monolayers.

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Section: Resultsmentioning

confidence: 99%

Surface Morphological Changes in Monolayers of Aromatic Polyamides Containing Various N-Alkyl Side Chains

Fujimori

Chiba²,

Sato³

et al. 2010

J. Phys. Chem. B

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“…Special attention was paid to carbonyl region between 162 and 172 ppm. The four carbonyl signals of roughly equal intensities appear, which are assigned to the four possible diads (HPPA–HPPA at 163.4 ppm, HPPA–SGA at 164.6 ppm, SGA–HPPA at 170.0 ppm, SGA–SGA at 171.3 ppm), suggesting the existence of random sequence for copolyesters 8, 11…”

Section: Resultsmentioning

confidence: 99%

“…The solubilities of copolyesters are given in Table IV. Homopolymers from HPPA, HBA, VA, or SGA are insoluble in organic solvents listed in Table IV,11, 12 while the solubility is increased dramatically for the copolyesters. This enhanced solubility behavior indicates that the copolyesters are random copolymers—neither a block copolymer nor a blend of two homopolymers as suggested by 13 C‐NMR spectra shown in Figure 3.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, and hydrolytic degradation of copolyesters of 3-(4-hydroxyphenyl) propionic acid andp-hydroxybenzoic acid, vanilic acid, or syringic acid

Nagata¹

2000

J. Appl. Polym. Sci.

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A series of copolyesters were prepared by a direct polycondensation of 3‐(4‐hydroxyphenyl) propionic acid and p‐hydroxybenzoic acid (HBA), vanilic acid (VA), or syringic acid (SGA) of different composition in pyridine using diphenyl chlorophosphate and lithium bromide as condensing agents. The effects of methoxy substitution in the benzene ring and copolymer composition on the synthesis and thermal properties as well as hydrolytic degradation were examined. The methoxy substitution increased a glass transition temperature and a solubility, while it decreased a crystallinity and a thermal stability. The HBA series copolyesters showed a homogenous nematic phase, while the VA and SGA series copolyestes neither revealed an anisotropic melt nor formed a mobile melt below around 350°C. The hydrolytic degradation of melt‐pressed films was performed in a 5% sodium hydroxide aqueous solution at 40°C to test a biodegradability of the copolyesters. HBA‐50 and HBA‐30 exhibited the much higher degradation rate than HBA‐70, showing that the aliphatic ester linkage was more degradable than aromatic one. The degradation rates of VA‐50 and SGA‐50 were remarkably slower than that of HBA‐50 due to the steric hindrance of the methoxy group in the ortho position. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 2474–2481, 2000

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“…The direct polycondensation of polyesters and polyamides has been recently paid considerable attention as a possible environmentally benign procedure for ‘green’ polymer chemistry. Numerous types of condensation reagents for the direct polycondensation had been developed so far 1–13. These direct polycondensations were carried out in homogeneous solutions, and the stoichiometries between the two functional groups in the polymerization system is of great importance in preparing high molecular weight polymers.…”

Section: Introductionmentioning

confidence: 99%

Direct synthesis of poly(4′‐oxy‐4‐biphenylcarbonyl) and poly(2‐oxy‐6‐naphthoyl) under nonstoichiometric conditions

Kohama

Kimura

Uchida

et al. 2004

Polymer International

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Direct synthesis of poly(4 -oxy-4-biphenylcarbonyl) (POBP) and poly(2-oxy-6-naphthoyl) (PON) was examined by polycondensation of 4 -hydroxy-4-biphenylcarboxylic acid (HBPA) and 2hydroxy-6-naphthoic acid (HNA) in the presence of 4-ethoxybenzoic anhydride or 2-naphthoic anhydride as condensation reagents. Polymerizations were carried out at 320 • C in aromatic solvents and liquid paraffin. POBP, having a number-average degree of polymerization (DPn) of 38, was obtained as platelike crystals at the molar ratio of HBPA and anhydride of 50 mol%. PON was also obtained as plate-like crystals but the DPn was only 13. HBPA and HNA were first converted to reactive acyloxyaromatic acid intermediates. Then the DPn was increased by means of reaction-induced crystallization of oligomers and subsequent solid-state polymerization via an acid-ester exchange under nonstoichiometric conditions caused by the monocarboxylic acid by-product. Even though the DPn of PON was not as high, direct polycondensation of HBPA and HNA proceeded successfully with aromatic anhydrides.

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Direct synthesis of poly(phenyl ester)s by using triphenyl‐phosphine and carbon tetrachloride as condensing agents

Cited by 14 publications

References 6 publications

Surface Morphological Changes in Monolayers of Aromatic Polyamides Containing Various N-Alkyl Side Chains

Surface Morphological Changes in Monolayers of Aromatic Polyamides Containing Various N-Alkyl Side Chains

Synthesis, characterization, and hydrolytic degradation of copolyesters of 3-(4-hydroxyphenyl) propionic acid andp-hydroxybenzoic acid, vanilic acid, or syringic acid

Direct synthesis of poly(4′‐oxy‐4‐biphenylcarbonyl) and poly(2‐oxy‐6‐naphthoyl) under nonstoichiometric conditions

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