Soluble Biobased Polyimides from Diaminotruxinic Acid with Unique Bending Angles

Abstract

Biobased diamines with unique bending angles, βand δ-type truxinic acids, were prepared from functionalized 4nitrocinnamic acid derivatives via solid-state photodimerization and further chemical modification. The obtained diamines were polymerized with tetracarboxylic acid dianhydrides to produce soluble polyimides via chemical imidization at a high efficiency. The obtained δ-type-based polyimides exhibited a high thermostability at 10% weight loss temperature of ∼415 °C and good solubility in organic solvents. Most of the polyimides were soluble in chloroform and dichloromethane, as well as polar organic solvents. Tensile test results showed that biopolyimide films from cyclobutanetetracarboxylic dianhydride exhibited ∼10.2% elongation at break, indicating high flexibility.

Soluble and cross-linkable polyimides from a vanillin-derived diamine: preparation, post-polymerization and properties

“…[22][23][24][25] Since the properties of PIs are highly dependent on the chemical structures of dianhydrides and diamines, improved synthesis methodology of monomers with unique structures continues to drive the development of high-performance PI materials. [26][27][28] Recent studies have shown that incorporating of aromatic linkers with unique bending angles (including triarylamine, triarylmethane, spirobisbenzoxazole, and cinnamoyl photodimer-based structures [29][30][31][32][33][34][35][36][37][38][39] ) is becoming an effective approach to produce PIs with twisted backbones, which can improve the transparency and insulating properties through the decrease of interchain packing and increase of free volume. 38,40 In order to achieve a facile synthesis of PI with favorable processability, good transparency high thermal stability and mechanical strength, a novel triarylmethane-based diamine (DA-TFVE) with cross-linkable trifluorovinyl-ether (TFVE) groups was designed and successfully synthesized in this work (Fig.…”

“…Since the properties of PIs are highly dependent on the chemical structures of dianhydrides and diamines, improved synthesis methodology of monomers with unique structures continues to drive the development of high-performance PI materials. 26–28 Recent studies have shown that incorporating of aromatic linkers with unique bending angles (including triarylamine, triarylmethane, spirobisbenzoxazole, and cinnamoyl photodimer-based structures 29–39 ) is becoming an effective approach to produce PIs with twisted backbones, which can improve the transparency and insulating properties through the decrease of interchain packing and increase of free volume. 38,40…”

Upcycling Waste Thermosetting Polyimide Resins into High‐Performance and Sustainable Low‐Temperature‐Resistance Adhesives

“…However, both thermosetting and thermoplastic PI are hard to decompose for their features, resulting in serious environmental pollution and resource waste. [2,4,5] Up to now, the researches on PI recycling mainly focus on thermoplastic PI. For example, thermoplastic PI is ground into powder and used as additive to improve the mechanical properties and frictional resistance of base material, but the value-added is low.…”

“…However, both thermosetting and thermoplastic PI are hard to decompose for their features, resulting in serious environmental pollution and resource waste. [ 2,4,5 ]…”

Terphenyl-based colorless and heat-resistant polyimides with a controlled molecular structure using methyl side groups

“…), bulky pendant moieties, and building asymmetrical or noncoplanar structures (kink, spiro and cardo). [5][6][7][8][9][10][11][12][13][14][15] Unfortunately, such structural manipulations rarely result in a satisfactory performance since the disturbing of self-chain alignment and loosening of the chain stacking of aromatic polyimides will inevitably lead to the loss of their inherent properties, including, a significant decrease of the packing density arising from -CF 3 in both diamines and dianhydrides, 16,17 an unacceptable glass transition temperature (T g ) (<350 °C, differential scanning calorimetry (DSC); <400 °C, dynamic mechanical analyses (DMA); see Table S1 †) due to bulky pendant moieties, 13,18 a decline in decomposition temperature (T d5 , 365-470 °C) due to the incorporation of alicyclic structures, 11,[19][20][21] unacceptable coefficients of thermal expansion (up to 83 ppm K −1 ) due to the destruction of linear and rigid structures (cycloaliphatic), 22 and a limited effect on color elimination caused by the introduction of large aromatic pendant groups. 23 Therefore, an optimal molecular design to balance the thermal and optical properties of CPIs remains the current primary goal.…”