New aromatic polyamides and polyimides having an adamantane bulky group

Abstract

This paper reports the synthesis and characterization of a new rigid diamine monomer, having a spiro carbon moiety and an adamantane bulky group in its structure; namely spiro-(adamantane-2,9′(2',7'-diamino)-fluorene) (SADAF). After its synthesis, using a straightforward methodology, a novel family of aromatic polyimides (PIs) and polyamides (PAs) has been attained by reaction of SADAF with three aromatic dianhydrides and two diacid chlorides, respectively. Two of the polyimides were obtained through the formation of the corresponding polyamic acid and subsequent thermal cycloimidization, whereas the other one, the polyimide from SADAF and 2,2bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), could be synthesized by chemical imidization from the polyamic precursor. Regarding polyamides, two new ones, made from SADAF and isophthaloyl chloride (IPC) and the diacid chloride of 2,2bis(4-carboxyphenyl)hexafluoropropane (6FC) could be obtained. All the polymers showed high Tg, above 350 ºC, and excellent thermal resistance, with onset degradation temperatures higher than 450 ºC. Polymers formed by the combination of SADAF with 6FDA and 6FC were prepared as dense films with good mechanical properties and their permselectivity properties were measured.

Advances in studies of thermal degradation of polymeric materials Part I. Literature studies

“…Wykazują one doskonałą stabilność termiczną, dobre właściwości mechaniczne, zwiększoną odporność chemiczną i wysoką temperaturę zeszklenia. PlazaLozano [83] badał syntezę i właściwości nowych polimerów tego typu otrzymanych z monomerów, do których wprowadzono fluoren (tricykliczny węglowodór aromatyczny), spirany (pierścienie węglowodorowe połą-…”

Functional Aromatic Polyamides

“…Similar studies were with aromatic polyamides containing 1-adamantanemethoxy substituted triphenylamine and the obtained membranes to analyze gas separation processes. Plaza-Lozano et al [75] reported the synthesis of polyamides and polyimides with high T g values above 350 • C and onset degradation temperatures higher than 450 • C. Polymers were prepared from a rigid diamine monomer, namely spiro-(adamantane-2,9 (2 ,7 -diamino)-fluorene) (Scheme 15, P30). The values of permeability and selectivity showed well-balanced gas productivity, in particular for the CO 2 /CH 4 separation.…”

Polyimides with side groups: Synthesis and effects of side groups on their properties

“…In addition, alicyclic units are introduced into diamines as side groups to prepare some special polyimides. For example, Plaza‐Lozano et al synthesized a diamine 20 with an adamantane side group through the nitration and hydrogenation reduction with Pd/C as shown in Scheme …”

“…Generally, the gas permeability of polyimide films can be increased by improving the fractional free volume (FFV). It is a good approach to increase the FFV of polyimides by introducing side groups into polyimide backbone, including phenyl, tert ‐butyl, and alicyclic units . However the gas permselectivity decrease with increasing FFV correspondingly; that is, the polyimide gas separation membranes still suffer from a trade‐off between gas permeability and permselectivity.…”