Cyclopolycondensation. XIII. Polymer Reactions of Polybenzoxazinones with Organic Base

Kurihara, Masaru; Hagiwara, Yoshichi

doi:10.1295/polymj.1.425

Cited by 6 publications

(2 citation statements)

References 11 publications

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“…Previously poly(quinazolinone)s have been synthesized by heating an aromatic diamine and a bis(amic acid) or by a reaction of polybenzoxazinones with primary amines followed by cyclization by heating in the presence of an inorganic salt such as lithium chloride …”

Section: Introductionmentioning

confidence: 99%

“…Previously poly(quinazolinone)s have been synthesized by heating an aromatic diamine and a bis(amic acid) 32 or by a reaction of polybenzoxazinones with primary amines followed by cyclization by heating in the presence of an inorganic salt such as lithium chloride. 33 In this paper, we describe the synthesis of a novel heterocyclic diamine monomer, 2-(4-aminophenyl)-6amino-4(3H)-quinazolinone. Polyimides from this amine would be expected to form high modulus films because of the rigid quinazolinone moiety and hydrogen bonding forming ablity of the quinazolinone.…”

Section: Introductionmentioning

confidence: 99%

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Polyimides Containing a Quinazolinone Moiety

Yoshida

Hay

1997

Macromolecules

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A novel heterocyclic diamine monomer, 2-(4-aminophenyl)-6-amino-4(3H)-quinazolinone was synthesized from readily available compounds in three steps in high yield. A series of novel polyimides containing the quinazolinone moiety were synthesized either by a one-step solution polymerization reaction or by a two-step procedure that included a ring-opening polyadddition to give poly(amic acid)s, followed by cyclodehydration to polyimides. In the one-step method in m-cresol or p-chlorophenol with isoquinoline catalyst, polyimides with inherent viscosities of 0.44−0.63 dL/g were obtained. Polyimides 4f and 4g from dianhydrides which have a flexible linkage, hexafluoroisopropylidene dianhydride (2f) and BPA dianhydride (2g), were soluble in hot m-cresol and could be cast into tough films from m-cresol solution. In the two-step method, poly(amic acid)s with inherent viscosity between 0.63 and 1.40 dL/g were obtained in DMAc at room temperature. The poly(amic acid)s were converted to the corresponding polyimide films by thermal cyclodehydration. The T g values of the polyimides ranged from 298 to 350 °C. Polyimide 4a from pyromellitic dianhydride (2a) did not show a clear transition in the DSC. Polyimides 4b from biphenyltetracarboxylic dianhydride (2b) and 4g were semicrystalline and showed clear endothermic peaks for T m at 465 and 356 °C, respectively. Degradation temperatures for 5% weight loss all occurred above 540 °C in nitrogen and above 537 °C in air. Young's moduli of thin films ranged from 2.34 to 4.89 GPa at room temperature and they maintained the high moduli to high temperatures. The monomer was successufuly copolymerized with 4,4‘-oxydianiline and 2g. With increasing incorporation of quinazolinone units, the copolymers had higher T g values, were more thermally stable, and had higher moduli.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polyimides Containing a Quinazolinone Moiety

Yoshida

Hay

1997

Macromolecules

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Thermal degradation of polymers. Part XIX. The thermal cyclization and characterization of quinazolone pre‐polymers

Chan¹,

Still²

1978

J of Applied Polymer Sci

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SynopsisA series of pre-polymers prepared from 4,4'-diaminodiphenyl-3,3'dicarboxylic acid and aromatic diacetamido compounds have been thermally cyclized and their structures have been investigated using infrared spectroscopy, combustion analysis, and weight loss techniques. The structures obtained on cyclization are discussed in terms of concurrent cyclization and decarboxylation reactions resulting in incomplete cyclization. Specific structural features due to the lability of main chain bonds at the cyclization temperatures are also discussed. Dynamic thermogravimetry and isothermal weight loss studies have been used to evaluate thermal stability and kinetic parameters. The results are discussed in terms of the overall complexity of the polymer structure and the complexity of the degradation process. It is concluded that in such systems, where the structural variations are large, it is not possible to define a meaningful stability sequence because like systems are not under comparison.

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Thermal degradation of polymers. Part XX. The effect of thermal ageing on thermal diffusivity and hardness of polyquinazolones

Chan¹,

Still²

1978

J of Applied Polymer Sci

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SynopsisPre-polymers prepared from 4,4'-diaminodiphenyl-3,3'-dicarboxylic acid and aromatic diacetamido compounds have been cyclized under optimized conditions. The thermal diffusivity and hardness of these materials have been evaluated. The effect of thermal ageing on these parameters and weight loss has also been investigated. Changes in these parameters have been related to the possible structural changes occurring within these systems. These changes are discussed in terms of the potential use of these materials in tribological applications.

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Cyclopolycondensation. XIII. Polymer Reactions of Polybenzoxazinones with Organic Base

Cited by 6 publications

References 11 publications

Polyimides Containing a Quinazolinone Moiety

Polyimides Containing a Quinazolinone Moiety

Thermal degradation of polymers. Part XIX. The thermal cyclization and characterization of quinazolone pre‐polymers

Thermal degradation of polymers. Part XX. The effect of thermal ageing on thermal diffusivity and hardness of polyquinazolones

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