Synthesis and properties of poly(amide-imide)s based on N,N′-bis(4-carboxyphenyl)-4,4′-oxydiphthalimide, p-aminobenzoic acid and various aromatic diamines

Chin Ping Yang, Ruei Shin Chen, Kuei Shi Hung, Eamor Woo

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A new diimide-diacid monomer, N,N′ -bis(4-carboxyphenyl)-4,4′-oxydiphthalimide (I), was prepared by azeotropic condensation of 4,4′-oxydiphthalic anhydride (ODPA) and p-aminobenzoic acid (p-ABA) at a 1:2 molar ratio in a polar solvent mixed with toluene. A series of poly (amide-imide)s (PAI, IIIa-m) was synthesized from the diimide-diacid I (or I′, diacid chloride of I) and various aromatic diamines by direct polycondensation (or low temperature polycondensation) using triphenyl phosphite and pyridine as condensing agents. It was found that only IIIk-m having a meta-structure at two terminals of the diamine could afford good quality, creasable films by solution-casting; other PAIs III using diamine with para-linkage at terminals were insoluble and crystalline; though IIIg-i contained the soluble group of the diamine moieties, their solvent-cast films were brittle. In order to improve their to solubility and film quality, copoly(amide-imide)s (Co-PAIs) based on I and mixtures of p-ABA and aromatic diamines were synthesized. When on equimolar of p-ABA (m=1) was mixed, most of Co-PAIs IV had improved solubility and high inherent viscosities in the range 0.9-1.5 dl g-1; however, their films were still brittle. With m=3, series V was obtained, and all members exhibited high toughness. The solubility, film-forming ability, crystallinity, and thermal properties of the resultant poly(amide-imide)s were investigated.

Original languageEnglish
Pages (from-to)406-416
Number of pages11
JournalPolymer International
Volume51
Issue number5
DOIs
Publication statusPublished - 2002 May 1

Fingerprint

Imides
4-Aminobenzoic Acid
Diamines
Polyamideimides
Amides
Acids
Solubility
Polycondensation
Anhydrides
Toluene
Pyridine
Toughness
Chlorides
Condensation
Casting
Thermodynamic properties
Monomers
Viscosity
Crystalline materials

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

@article{a8d9d46e86224ba59f5bb20683d368f8,
title = "Synthesis and properties of poly(amide-imide)s based on N,N′-bis(4-carboxyphenyl)-4,4′-oxydiphthalimide, p-aminobenzoic acid and various aromatic diamines",
abstract = "A new diimide-diacid monomer, N,N′ -bis(4-carboxyphenyl)-4,4′-oxydiphthalimide (I), was prepared by azeotropic condensation of 4,4′-oxydiphthalic anhydride (ODPA) and p-aminobenzoic acid (p-ABA) at a 1:2 molar ratio in a polar solvent mixed with toluene. A series of poly (amide-imide)s (PAI, IIIa-m) was synthesized from the diimide-diacid I (or I′, diacid chloride of I) and various aromatic diamines by direct polycondensation (or low temperature polycondensation) using triphenyl phosphite and pyridine as condensing agents. It was found that only IIIk-m having a meta-structure at two terminals of the diamine could afford good quality, creasable films by solution-casting; other PAIs III using diamine with para-linkage at terminals were insoluble and crystalline; though IIIg-i contained the soluble group of the diamine moieties, their solvent-cast films were brittle. In order to improve their to solubility and film quality, copoly(amide-imide)s (Co-PAIs) based on I and mixtures of p-ABA and aromatic diamines were synthesized. When on equimolar of p-ABA (m=1) was mixed, most of Co-PAIs IV had improved solubility and high inherent viscosities in the range 0.9-1.5 dl g-1; however, their films were still brittle. With m=3, series V was obtained, and all members exhibited high toughness. The solubility, film-forming ability, crystallinity, and thermal properties of the resultant poly(amide-imide)s were investigated.",
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Synthesis and properties of poly(amide-imide)s based on N,N′-bis(4-carboxyphenyl)-4,4′-oxydiphthalimide, p-aminobenzoic acid and various aromatic diamines. / Yang, Chin Ping; Chen, Ruei Shin; Hung, Kuei Shi; Woo, Eamor.

In: Polymer International, Vol. 51, No. 5, 01.05.2002, p. 406-416.

Research output: Contribution to journalArticle

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AU - Yang, Chin Ping

AU - Chen, Ruei Shin

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AU - Woo, Eamor

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N2 - A new diimide-diacid monomer, N,N′ -bis(4-carboxyphenyl)-4,4′-oxydiphthalimide (I), was prepared by azeotropic condensation of 4,4′-oxydiphthalic anhydride (ODPA) and p-aminobenzoic acid (p-ABA) at a 1:2 molar ratio in a polar solvent mixed with toluene. A series of poly (amide-imide)s (PAI, IIIa-m) was synthesized from the diimide-diacid I (or I′, diacid chloride of I) and various aromatic diamines by direct polycondensation (or low temperature polycondensation) using triphenyl phosphite and pyridine as condensing agents. It was found that only IIIk-m having a meta-structure at two terminals of the diamine could afford good quality, creasable films by solution-casting; other PAIs III using diamine with para-linkage at terminals were insoluble and crystalline; though IIIg-i contained the soluble group of the diamine moieties, their solvent-cast films were brittle. In order to improve their to solubility and film quality, copoly(amide-imide)s (Co-PAIs) based on I and mixtures of p-ABA and aromatic diamines were synthesized. When on equimolar of p-ABA (m=1) was mixed, most of Co-PAIs IV had improved solubility and high inherent viscosities in the range 0.9-1.5 dl g-1; however, their films were still brittle. With m=3, series V was obtained, and all members exhibited high toughness. The solubility, film-forming ability, crystallinity, and thermal properties of the resultant poly(amide-imide)s were investigated.

AB - A new diimide-diacid monomer, N,N′ -bis(4-carboxyphenyl)-4,4′-oxydiphthalimide (I), was prepared by azeotropic condensation of 4,4′-oxydiphthalic anhydride (ODPA) and p-aminobenzoic acid (p-ABA) at a 1:2 molar ratio in a polar solvent mixed with toluene. A series of poly (amide-imide)s (PAI, IIIa-m) was synthesized from the diimide-diacid I (or I′, diacid chloride of I) and various aromatic diamines by direct polycondensation (or low temperature polycondensation) using triphenyl phosphite and pyridine as condensing agents. It was found that only IIIk-m having a meta-structure at two terminals of the diamine could afford good quality, creasable films by solution-casting; other PAIs III using diamine with para-linkage at terminals were insoluble and crystalline; though IIIg-i contained the soluble group of the diamine moieties, their solvent-cast films were brittle. In order to improve their to solubility and film quality, copoly(amide-imide)s (Co-PAIs) based on I and mixtures of p-ABA and aromatic diamines were synthesized. When on equimolar of p-ABA (m=1) was mixed, most of Co-PAIs IV had improved solubility and high inherent viscosities in the range 0.9-1.5 dl g-1; however, their films were still brittle. With m=3, series V was obtained, and all members exhibited high toughness. The solubility, film-forming ability, crystallinity, and thermal properties of the resultant poly(amide-imide)s were investigated.

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