Synthesis and structural studies of new copolyimides 2. Influence of pyromellitimide rings on copolymer structure

Abstract

The reaction of pyromellitic dianhydride (1,2 : 4,5-benzenetetracarboxylic dianhydride) (1) with L-and D-alanine ( 2~) and ( 2~) leads to new monomers which were used to synthesize new copolymers. These copolymers were obtained as a product of the condensation of optical isomers of bis[N-(1 -chloroformylethyl)]pyromellitimides (CFEP) with poly(ethy1ene glycol) PEG-2000 (5). The effect of monomer structure on the structure and thermal properties of the polymers was studied using X-ray diffraction, differential scanning calorimetry and thermogravimetry. The copolymers were compared with similar copolyimides obtained previously from bis(N-chloro-formylmethy1)pyromellitimide and poly(ethy1ene glycol), PEG 2000. The dominating effect of poly(ethy1ene glycol) comonomer on the crystallinity, structure and thermal stability of these new copolymers is proven.

Synthesis and characterization of novel aromatic-aliphatic poly(amide-imide-imide)s (PAII)

“…In the first step, TMI-GTAn which was a precursor of TMIAc-GTAn, was obtained by a condensation reaction of TMA with L-glutamic acid 11) . In the second step, TMIAc-GTAn was synthesized by treatment of TMI-GTAn with excess thionyl chloride [5][6][7] . In detail, TMI-GTAn was synthesized from the reaction of trimellitic anhydride with glutamic acid as shown in Scheme 1.…”

“…In conclusion, those have better solubilities than polyimides containing pyromellitimide and glutamimide units or the representative PAI, Torlan 11) . It was reported that the aromatic-aliphatic poly-(iminoamic acid)s prepared from N-(pyromellitimino) diglutamic anhydride have excellent storage stabilities either in solution or in solid state in contrast to the aromatic poly-(amic acid)s prepared from pyromellitic anhydride [4][5][6][7]11) . This is also expected in case of PAIIs described in this report.…”

“…To attain thermoplasticity polyimides have been modified either through the addition of a side chain or through introduction of flexible, non-symmetrical and thermally stable linkages to the backbone. Among these modifications, natural amino acids have been used for the preparation of polyimides with either polyether, polyester or polyamides [3][4][5][6][7][8][9] . The combination of amide and imide groups which results in poly(amide-imide)s [PAI] imparts flexibility, elongation and toughness.…”

New optically active poly(esterimides) and poly(amideimides). Part I. Synthesis of optically active monomers

“…Syntezy prowadzono w zestawie aparaturowym sk³adaj¹cym siê z okr¹g³odennej kolby trójszyjnej zaopatrzonej w mieszad³o mechaniczne, ch³odnicê zwrotn¹, termometr oraz p³aszcz grzejny. Pos³u¿ono siê czterema metodami, opracowanymi na podstawie danych literaturowych dotycz¹cych podobnych syntez [11][12][13].…”

“…Dostêpna literatura zawiera niewiele tylko doniesieñ odnosz¹cych siê do optycznie czynnych PI. Pojedyncze publikacje dotycz¹ optycznie czynnych poli(eteroimidów) otrzymywanych z optycznie czynnego dibezwodnika 2,2'-bis(3,4-dikarboksyfenoksy)-1,1'-binaftalenowego oraz amin aromatycznych w typowej dwuetapowej metodzie obejmuj¹cej reakcjê polikondensacji i cyklodehydratacjê [10], a tak¿e optycznie czynnych poli(estroimidów) uzyskiwanych z glikolu polioksyetylenowego oraz produktów reakcji bezwodnika piromelitowego i D-oraz L-alaniny [11].…”