Synthesis and characterization of fully aliphatic polyimides from an aliphatic dianhydride with piperazine spacer for enhanced solubility, transparency, and low dielectric constant

Abstract

A new series of fully aliphatic polyimide (API) based on a novel aliphatic dianhydride monomer-2,2 0 -(1,4-piperazinediyl)-disuccinic anhydride (PDA), in which two units of succinic anhydride have been connected by an aliphatic heterocyclic piperazine spacer that possesses aminomethylene (-NCH 2 ) moiety in the aliphatic/alicylic backbone capable of inducing charge transfer (CT) interactions in the polyimide network, was successfully synthesized. The APIs were soluble in common polar organic solvents. The polyimide films of PDA with alicyclic diamines were almost colorless. T 10 (temperature of 10% weight loss) of APIs were ranged from 299-418 C and T g of API3-API6 were in the temperature range of 170 to 237 C. The light-colored polyimide films of API3-API6 possessed good mechanical properties with tensile strength of 54-72 Mpa, tensile modulus of 1.6-2.3 Gpa and elongation at break of 4-9%. The polyimide films of API3-API6 were highly flexible and freestanding which is quite rare in fully APIs. The dielectric constant of one of the synthesized API (API4) was as low as 2.14.

Synthesis and properties of soluble aromatic polyimides from novel 4,5-diazafluorene-containing dianhydride

“…In the third stage, the bis(ether diacid) was subjected to a dehydration reaction in acetic anhydride to obtain the bis(ether andydride). Structures of the precursors and dianhydride monomer were determined by elemental analysis, 1 H NMR, 13 C NMR and FT-IR spectra.…”

“…[8][9][10][11] Generally, polyimides are synthesized by the polycondensation of diamine and dianhydride. Many approaches focused on structure modication (novel diamine and dianhydride), such as introducing aliphatic chains, 12,13 exible linkage, [14][15][16] nonplanar structure, [17][18][19][20] bulky CF 3 groups [21][22][23] and ring-shaped structures, 24 are developed to overcome the traditional PIs' drawbacks mentioned above. However, in most of the case, as the solubility and transmittance of PIs improved, the thermal properties and mechanical properties are sacriced.…”

Synthesis of novel biobased polyimides derived from isomannide with good optical transparency, solubility and thermal stability

“…However, it is difficult to modify the structures of these alicyclic monomers, thus to tune the performance of the resultant PIs. 22 Thereof, the synthesis of optically transparent PIs with excellent combined properties is still a great challenge. For the second strategy, whereas, alicyclic dianhydrides or diamines can be facilely prepared, based on alicyclic moieties containing reactive groups; furthermore, it can combine different functional units such as trifluoromethyl group (CF 3 ), to form more desirable monomers.…”

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

“…As shown in Scheme , the piperazine‐containing alicyclic dianhydride monomer (PDA) was obtained through a four‐step synthetic route . The first step involved the synthesis of dimethyl fumerate (DMF) which underwent Michael addition reaction in the second step with piperazine to yield 1,4‐piperazinediyl‐tetramethyldisuccinate (PDSTE).…”