Preparation and properties of new soluble aromatic polyamides from 2,2?-bis(4-aminophenyl)biphenyl and aromatic dicarboxylic acids

Liou, Guey‐Sheng; Maruyama, Makoto; Kakimoto, Masa–aki; Imai, Yoshio

doi:10.1002/(sici)1099-0518(19980915)36:12<2029::aid-pola8>3.0.co;2-s

Cited by 13 publications

(7 citation statements)

References 16 publications

(21 reference statements)

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“…Highly ordered aromatic polyamides, in particular, those prepared from symmetrical monomers, can develop high crystallinity, a factor that promotes insolubility. Thus, research efforts have been directed mainly toward structural modifications designed to hinder regularity and chain packing 3–7. Strong molecular interactions through hydrogen bonding of amide groups are also responsible for the remarkable intractability, and chemical modifications must take this aspect into consideration to introduce groups that provide chain separation, and consequently, higher free volume and solubility 8–13…”

Section: Introductionmentioning

confidence: 99%

Polyisophthalamides with heteroaromatic pendent rings: Synthesis, physical properties, and water uptake

Ferreiro

Campa

Lozano

et al. 2005

J. Polym. Sci. A Polym. Chem.

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A set of novel aromatic polyamides containing pyridine pendent groups was prepared from aromatic diamines and new monomers that are 5-substituted derivatives of isophthalic acid bearing nicotinamide, isonicotinamide, or picolinamide groups. The polymers were obtained in high yield and high molecular weight by the phosphorylation method of polycondensation. They were characterized by spectroscopic and chromatographic methods and several of their properties were investigated. All of the polymers were soluble in polar aprotic solvents and gave films of good mechanical properties. Glass transition temperatures were higher than that of the reference polymer, poly(m-phenyleneisophthalamide) (IP-MPD), while the thermal resistance, defined by the initial decomposition temperature observed by thermogravimetry, was in the range 370-420 8C, lower by 30-70 8C than that of IP-MPD. The presence of a pendent pyridine group and an additional amide side group per repeat unit made the polymers essentially amorphous and greatly improved their abilities to absorb water in comparison with nonsubstituted polyamides. Water uptake values up to 15% were observed at 65% relative humidity. V V C 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5300-5311, 2005

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Section: Introductionmentioning

confidence: 99%

Polyisophthalamides with heteroaromatic pendent rings: Synthesis, physical properties, and water uptake

Ferreiro

Campa

Lozano

et al. 2005

J. Polym. Sci. A Polym. Chem.

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“…However, these polymers are generally intractable and lack the properties essential for successful fabrication into useful forms because of their high melting or glass‐transition temperatures ( T g 's) and their limited solubility in organic solvents 2. Therefore, a great deal of effort has been expended to improve the processing characteristics of the relatively intractable polymers 3–8. These studies include introducing flexible segments into the polymer chain; replacing symmetrical aromatic rings with unsymmetrical ones, which leads to a reduction in crystallinity; introducing bulky pendant groups to minimize crystallization; and forming a noncoplanar structure, thereby making crystallization impossible.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of aromatic poly(ester amide)s with pendant phosphorus groups

Liou

Hsiao

2002

J. Polym. Sci. A Polym. Chem.

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Two series of phosphorus-containing aromatic poly(ester amide)s with inherent viscosities of 0.46 -3.20 dL/g were prepared by low-temperature solution polycondensation from 1,4-bis(3-aminobenzoyloxy)-2-(6-oxido-6H-dibenz͗c,e͗͘1,2͘oxaphosphorin-6-yl)naphthalene and 1,4-bis(4-aminobenzoyloxy)-2-(6-oxido-6H-dibenz͗c,e͗͘1,2͘oxaphosphorin-6-yl)naphthalene with various aromatic diacid chlorides. All the poly(ester amide)s were amorphous and readily soluble in many organic solvents, such as N, N-dimethylformamide, N,N-dimethylacetamide (DMAc), and N-methyl-2-pyrrolidone (NMP). Transparent, tough, and flexible films of these polymers were cast from DMAc and NMP solutions. Their casting films had tensile strengths of 71-214 MPa, elongations to break of 5-10%, and initial moduli of 2.3-6.0 GPa. These poly(ester amide)s had glass-transition temperatures of 209 -239°C (m-series) and 222-267°C (p-series). The degradation temperatures at 10% weight loss in nitrogen for these polymers ranged from 462 to 489°C, and the char yields at 800°C were 55-63%. Most of the poly(ester amide)s also showed a high char yield of 35-45%, even at 800°C under a flow of air. The limited oxygen indices of these poly(ester amide)s were 35-46.

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“…In the past worked polyamides derived from biphenyl unit containing monomer by adding substituent at 2 2ʹ position on biphenyl such as methyl, cyano, phenyl, halogen, sulfonic acid and trifluoromethyl phenoxy groups [ 16–19 ]. The bulky phenyl and naphthyl units incorporated at the 2,2ʹ substituted position of biphenylene as pendant groups could reduce the interchain interaction of the polymers, packing efficiency, crystallinity and increases free volume to enhance the solubility of polymers with retention of high thermal stability [ 20–22 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and properties of novel polyamides derived from 4 4ʹ bis(4-carboxy methylene) biphenyl and various diamines

Ghodke

Tamboli

Diwate

et al. 2020

Designed Monomers and Polymers

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Novel aromatic aliphatic diacid monomer, 4 4ʹ bis(4-carboxy methylene) biphenyl was synthesized via friedel craft acylation with acetic anhydride followed by willgerodot reaction and used in the preparation of polyamides by direct polycondensation using the Yamazaki phosphorylation reaction with commercial aromatic diamines. These polyamides were obtained in good yield with moderate-to-high-molecular-weight build up as evidenced by inherent viscosities in the range of 0.52–0.96 dlg−1. The XRD studies showed that all the polyamides were amorphous in nature and these polymers dissolved in polar aprotic solvents such as N-methyl-2-pyrrolidone(NMP),N,N-dimethylsulfoxide(DMSO), N,N-dimethyl formamide (DMF) and N,N-dimethyl acetamide. The resulting polyamides were characterized by inherent viscocity measurements, FT-IR, 1H NMR and 13C NMR spectroscopy, solubility, thermogravimetry, X-ray diffraction studies. These polyamides had glass transition temperatures between 210°C and 261°C, and their temperatures at a 10% weight loss were 620 to 710°C and 497 to 597°C in nitrogen and air atmospheres, respectively, which indicates thermally stable polymers.

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Preparation and properties of new soluble aromatic polyamides from 2,2?-bis(4-aminophenyl)biphenyl and aromatic dicarboxylic acids

Cited by 13 publications

References 16 publications

Polyisophthalamides with heteroaromatic pendent rings: Synthesis, physical properties, and water uptake

Polyisophthalamides with heteroaromatic pendent rings: Synthesis, physical properties, and water uptake

Synthesis and properties of aromatic poly(ester amide)s with pendant phosphorus groups

Synthesis, characterization and properties of novel polyamides derived from 4 4ʹ bis(4-carboxy methylene) biphenyl and various diamines

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