Synthesis and characterization of new soluble and thermally stable poly(amide‐imide)s containing pendent benzimidazole moieties

Abstract

Preparation of new types of poly(amideimide)s with high thermal stability and improved solubility was investigated. Two new diimide-dicarboxylic acid containing pendent benzimidazole group, viz., 2-[3,5-bis(N-trimellitimidoyl)-phenyl] benzimidazole (DIDA-i) and 2-[3,5-bis(N-trimellitimidoyl)-phenyl] 5-methyl benzimidazole (DIDA-ii) from the condensation of 5-(2-benzimidazole)-1,3-phenylenediamine (DABI A ) and 5-(5-methyl-2-benzimidazole)-1,3-phenylenediamine (DABI B ) with trimellitic anhydride in glacial acetic acid were synthesized, respectively. 1,3-bis(N-trimellitimidoyl)benzene (DIDA-iii, as a reference) was also synthesized in a similar manner to study the properties of the its structure. Three series of aromatic poly(amide-imide)s were prepared by triphenyl phosphite-activated polycondensation from diimide-dicarboxylic acid DIDA-i, DIDA-ii, and the reference monomer DIDA-iii with various aromatic diamines. The polymers were obtained in quantitative yields with inherent viscosities between 0.46 and 0.81 dL g À1. The effects of the benzimidazole pendent groups on the polymer properties, such as solubility and thermal stability were investigated by comparison of the polymers. The polymers bearing benzimidazole pendent groups exhibited thermal stability and good solubility in common polar solvents higher than the reference polymers.

Preparation of soluble polysilsesquioxane containing phthalimido side-chain groups and its optical and thermal properties

“…Conversely, some polymers containing imido side-chain groups that are thermally stable, e.g., phthalimido groups, show high thermal stability, solubility, and processability. For example, polyamides [3,4], polyesters [5], poly(amide-imide)s [6,7], poly(benzimidazole-amide)s [8], poly(ester-imide)s [9], poly(urethane-imide)s [10], and polynorbornenes [11] bearing phthalimido pendent groups indicated excellent thermal properties while maintaining solubility. Thus, most of the polymers bearing phthalimido side-chain groups possess organic main-chains.…”

Fabrication and characterization of poly(benzimidazole-amide)/functionalized titania nanocomposites containing phthalimide and benzimidazole pendent groups

“…Compound N-[3,5-bis(5-carboxylic acid-2-benzimidazole) phenyl]phthalimide (3) containing pendent phthalimide group has been previously synthesized through a three-step synthetic procedure starting from 5-amino isophthalic acid and phthalic anhydride outlined in Scheme 1 [40]. First, the 5-(Nphthalimide)isophthalic acid (1) was prepared via a ringopening addition of 5-amino isophthalic acid with one equivalent amount of phthalic anhydride in an amide-type polar solvent, followed by cyclodehydration by means of toluenewater azeotropic distillation.…”

“…(3-Methacryloxypropyl)trimethoxysilane (MPS) (98 % purity, 1.045 g mL −1 , Aldrich) was used as received. 5-(2-Benzimidazole)-1,3-phenylenediamine (4) was synthesized as described previously [40]. (3) was synthesized by using three-step procedure as described previously [39].…”

Design and Characterization of Chiral and Thermally Stable Nanostructure Poly(amide-imide)s Containing Different Trimellitylimido-Amino Acid-Based Diacids and 4,4′-Methylenebis(3-chloro-2,6-diethylaniline) Units

“…They bring together the superior mechanical properties associated with amide groups and the high thermal stability determined by imide rings. These properties put PAIs at the top of the price and performance pyramid [4][5][6] . Among the PAIs, type of chiral is important polymers in macromolecular science because the majority of bioorganic molecules are chiral.…”