Aromatic polyamides with imide pendent groups

Abstract

Aromatic polyamides with imide pendent groups were prepared from 4,4'-diaminodiphenylether and imide-diacid chlorides by solution polycondensation. Imidediacid chlorides used included the diacid chlorides of 5-maleimidoisophthalic, 5-dichloromaleimidoisophthalic, 5-tetrahydrophthalimidoisophthalic, 5-chlorendimidoisophthalic, 5-nadimidoisophthalic, 5-methylnadimidoisophthalic and 5-phthalimidoisophthalic acid. The pure aromatic polyamide from 4,4'-diaminodiphenylether and isophthaloyl chloride was also prepared for comparative reasons.Polyamide-imides are soluble in polar organic solvents and show good thermal resistance. They are film-forming and the films have good mechanical properties. Those polyamide-imides which contain unsaturated carbon-carbon bonds may be crosslinked by heating to 220°C, giving rise to insoluble materials with improved mechanical resistance. ZUSAMMENFASSUNG:Aromatische Polyamide mit Imidseitengruppen wurden aus 4,4 '-Diaminodiphenylether und Imid-Disaurechloriden durch Losungspolykondensation hergestellt. Die verwendeten Imid-Disaurechloride urnfafiten die Disaurechloride von 5-Maleinimidoisophthalsaure, 5-Dichlormaleinimidoisophthalsaure, 5-Tetrahydrophthalimidoisophthalsaure, 5-Hexachlorendomethylentetrahydrophthalimidoisophthalsaure, 5-Endomethylentetrahydrophthalimidoisophthals&ue, 5-Methylenendomethylentetrahydrophthalimidoisophthalsaure, und 5-Phthalimidoisophthalsaure. Das reine aromatische Polyamid aus 4,4 '-Diaminodiphenylether und Isophthaloylchlorid wurde zu Vergleichszwecken ebenfalls hergestellt.Polyamidimide sind in polaren organischen Losungsmitteln ldslich und zeigen gute thermische Bestandigkeit. Sie konnen Filme bilden, die gute mechanische Eigenschaften haben. Diejenigen Polyamidimide, die ungesattigte Kohlenstoff-Kohlenstoff-Bindungen enthalten, kiinnen durch Erhitzen auf 220 "C vernetzen und geben unlosliche Materialien mit verbesserter mechanischer Festigkeit.

Thermally Reversible Cross‐Linked Polyamides with High Toughness and Self‐Repairing Ability from Maleimide‐ and Furan‐Functionalized Aromatic Polyamides

“…[23][24][25][26][27][28][29][30] One polyamide modification approach is crosslinkable polyamides, which can be processed into thin films and other forms and then thermally or photochemically cross-linked. [31][32][33][34][35] De Abajo and coworkers [31,32] reported cross-linkable polyamides having reactive maleimide and phthalimide groups. Curable polyamides possessing pendent enaminonitrile groups were reported by Kim et al [33][34][35] Cross-linked polyamides showed improved thermal stability.…”

“…[31,32] The cross-linking reaction did not occur with the PA-F polymers which contained unreactive succinimidefuran groups instead of the reactive maleimide groups. Therefore, PA-MI and PA-F polymers exhibited different thermal degradation patterns as observed by thermogravimetric analysis ( decreased and that at 1 662 cm À1 (C --C in adduct) increased indicating the consumption of furan groups and formation of maleimide-furan adduct groups, respectively, during the maleimide-furan DA reaction.…”

Poly(m‐phenylene isophthalamides)‐containing nitro groups

“…The N,N-dimethylacetamide (DMA) used as solvent in the polycondensations was purified as reported earlier. 4 A typical polymerization was carried out by adding a mixture of 2.030 g (10 mmol) of isophthaloyl chloride and 2.480 g (10 mmol) of 5-nitroisophthaloyl chloride in several portions to a vigorously stirred solution of 2.163 g (20 mmol) of m-phenylenediamine and 2.0 g of LiCl in 50 mL of DMA a t -10°C After 1 h of stirring a t O°C and 2 h at 25OC, the reaction solution was cooled to 0°C and 6 mL (approx. 0.10 mol) of propylene oxide was added to neutralize the final viscous solution.…”

Synthesis and characterization of novel polyimides with bulky pendant groups

“…Introducing bulky pendant groups to modify the properties, particularly to improve the solubility, of aromatic and heterocyclic polymers is a general approach that has proved to be very efficient in many instances. [11][12][13][14][15][16] The results reported in the present study refer to novel polyimides prepared from dianhydrides containing -CObridging groups and bulky pendant units like phenyl or t-butyl. Monomers were designed also to contain metasubstituted phenylene groups in order to improve the solubility (processability) of the foreseen polymers.…”