Synthesis and properties of new halogen-substituted polyamides from 5-halo-m-phenylenediamines and both aliphatic and aromatic dicarboxylic acids

Kakimoto, Masa–aki; Yoneyama, Mitsuru; Imai, Yoshio

doi:10.1002/1099-0518(20001101)38:21<3911::aid-pola80>3.0.co;2-9

Cited by 7 publications

(2 citation statements)

References 21 publications

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“…These properties make them generally intractable or difficult to process, restricting their applications. Therefore, a great deal of effort has been expended to improve the processing characteristics of the relatively intractable polymers 3–14. 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 new soluble triphenylamine‐based aromatic poly(amine amide)s derived from N,N′‐bis(4‐carboxyphenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Liou

Hsiao

2002

J. Polym. Sci. A Polym. Chem.

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A new triphenylamine-containing aromatic dicarboxylic acid, N,NЈ-bis(4carboxyphenyl)-N,NЈ-diphenyl-1,4-phenylenediamine, was synthesized by the condensation of N,NЈ-diphenyl-1,4-phenylenediamine with 4-fluorobenzonitrile, followed by the alkaline hydrolysis of the intermediate dinitrile compound. A series of novel triphenylamine-based aromatic poly(amine amide)s with inherent viscosities of 0.50 -1.02 dL/g were prepared from the diacid and various aromatic diamines by direct phosphorylation polycondensation. All the poly(amine amide)s were amorphous in nature, as evidenced by X-ray diffractograms. Most of the poly(amine amide)s were quite soluble in a variety of organic solvents and could be solution-cast into transparent, tough, and flexible films with good mechanical properties. They had useful levels of thermal stability associated with glass-transition temperatures up to 280°C, 10% weight-loss temperatures in excess of 575°C, and char yields at 800°C in nitrogen higher than 60%.

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Section: Introductionmentioning

confidence: 99%

Synthesis and properties of new soluble triphenylamine‐based aromatic poly(amine amide)s derived from N,N′‐bis(4‐carboxyphenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Liou

Hsiao

2002

J. Polym. Sci. A Polym. Chem.

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“…[5][6][7][8] We have combined wide angle x-ray scattering ͑WAXS͒ and dielectric loss spectroscopy to get a deeper insight into the molecular structure-dynamics relationships.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure–dynamics relationships in glassy poly(isophthalamide)s as revealed by wide angle x-ray scattering, dielectric loss spectroscopy, and molecular modelling

Álvarez

Lozano

Abajo

et al. 2004

The Journal of Chemical Physics

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The effect of molecular structure on the gamma relaxation dynamics has been studied in a set of aromatic poly(isophthalamide)s. This polymer family differ in the bridge group between phenylene rings [hexafluoroisopropylidene (C(CF(3))(2)) or ether] and also in the presence of t-butyl groups (C(CH(3))(3)) as pendant substituent on the five position of isophthalic ring. The results obtained from wide angle x-ray scattering in the glassy state indicated that both (C(CF(3))(2)) and (C(CH(3))(3)) groups favor the separation between chains, which is reflected on different interchain average distances. Dielectric experiments showed that both bulky groups favor the mobility in the glassy state. Molecular modelling methods were used to know the kind of molecular motions associated to the dielectric relaxation observed below the glass transition temperature.

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Elaboration of rac‐Like Active Species from Lewis Base Functionalized Unbridged Zirconocenes for Isospecific Propylene Polymerization

Kim

Park

et al. 2008

Chemistry An Asian Journal

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A series of ortho or meta Lewis base functionalized unbridged zirconocenes, [{1-(E(n)-Ph)-3,4-Me(2)C(5)H(2)}(2)ZrCl(2)] (E = NMe(2), OMe; n = 1, 2), and a half-functionalized zirconocene, [{1-(p-Me(2)NC(6)H(4))-3,4-Me(2)C(5)H(2)}{1-(p-tolyl)-3,4-Me(2)C(5)H(2)}ZrCl(2)], were prepared. The crystal structures of these compounds determined by X-ray diffraction revealed the presence of only C(2)-symmetric rac-like isomers in the asymmetric units. In combination with methylaluminoxane (MAO) cocatalyst, the meta-functionalized complexes afforded mixtures of polymers that exhibit multimelting transition temperatures and broad molecular-weight distributions (MWDs) in propylene polymerization at atmospheric monomer pressure, whereas the ortho-functionalized complexes did not give rise to polymerization. Stepwise solvent extraction of the polymer mixtures showed that the polymers consist of amorphous, moderately isotactic, and highly isotactic portions, the weight ratio of which is dependent on the reaction temperature. (13)C NMR spectral analysis indicated that the [mmmm] methyl pentad value of the isotactic portion reached around 90%. Among the meta-functionalized zirconocenes, the di-OMe-substituted one afforded the largest amount of the isotactic portion at all temperatures, and the portion comprised 82 wt % of the crude polymer obtained at 25 degrees C. In contrast, propylene polymerization with the half-functionalized unbridged zirconocene resulted in the formation of nearly atactic polypropylene with a narrow MWD of around 2. These results corroborate the proposition that the rigid rac-like cation-anion ion pair of type [rac-L(2)ZrP](+)[Me-MAO](-) generated in situ, through Lewis acid-base interactions between the functional groups and [Me-MAO](-), is responsible for the isospecific propylene polymerization with the given class of functionalized unbridged zirconocenes and further indicate that the formation of such ion pairs can be favored by difunctionalization at the meta position of the phenyl ring with OMe groups.

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Synthesis and properties of new halogen-substituted polyamides from 5-halo-m-phenylenediamines and both aliphatic and aromatic dicarboxylic acids

Cited by 7 publications

References 21 publications

Synthesis and properties of new soluble triphenylamine‐based aromatic poly(amine amide)s derived from N,N′‐bis(4‐carboxyphenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Synthesis and properties of new soluble triphenylamine‐based aromatic poly(amine amide)s derived from N,N′‐bis(4‐carboxyphenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Molecular structure–dynamics relationships in glassy poly(isophthalamide)s as revealed by wide angle x-ray scattering, dielectric loss spectroscopy, and molecular modelling

Elaboration of rac‐Like Active Species from Lewis Base Functionalized Unbridged Zirconocenes for Isospecific Propylene Polymerization

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