Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

Abstract

4-(4-(4-(4-Aminophenoxy)-2-pentadecylphenoxy)phenoxy)aniline (APPPA) was synthesized starting from cashew nut shell liquid-derived bisphenol, i.e. 4-(4-hydroxyphenoxy)-3-pentadecylphenol, by nucleophilic substitution reaction with 4-chloronitrobenzene followed by reduction of the formed 4-(4-nitrophenoxy)-1-(4-(4-nitrophenoxy)phenoxy)-2pentadecylbenzene. Three new polyetherimides containing multiple ether linkages and pendent pentadecyl chains were synthesized by one-step high-temperature solution polycondensation of APPPA in m-cresol with three aromatic dianhydrides, i.e. 3,3 ′ ,4,4 ′ -oxydiphthalic anhydride, 4,4 ′ -(hexafluoroisopropylidene)diphthalic anhydride and 3,3 ′ ,4,4 ′ -biphenyltetracarboxylic dianhydride. Inherent viscosities and number-average molecular weights of the polyetherimides were in the ranges 0.66-0.70 dL g −1 and 17 100-29 700 g mol −1 (gel permeation chromatography, polystyrene standards), respectively, indicating the formation of reasonably high molecular weight polymers. The polyetherimides were soluble in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, pyridine, m-cresol, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and dimethylsulfoxide, and could be cast into transparent, flexible and tough films from their solutions in chloroform. The polyetherimides exhibited glass transition temperatures (T g ) in the range 113-131 ∘ C. The lowering of T g could be attributed to the combined influence of flexibilizing ether linkages and pentadecyl chains which act as 'packing-disruptive' groups. The temperature at 10% weight loss (T 10 ), determined from thermogravimetric analysis in nitrogen atmosphere, was in the range 460-470 ∘ C demonstrating good thermal stability. The virtues of solubility and large gap between T g and T 10 mean that the polyetherimides containing pendent pentadecyl chains have possibilities for both solution as well as melt processability.

Synthesis and properties of poly(arylene ether)s based on 3‐pentadecyl 4,4'‐biphenol

“…A broad reflection in the small angle region at about 2 θ ≈ 3° was observed for all poly(arylene ether)s which could be ascribed to the presence of a layered structure formed because of packing of pentadecyl chains. Similar observations were reported in previous work on pentadecyl‐chain‐containing poly(arylene ether)s, polyimides etc …”

Direct Creation of Highly Conductive Laser‐Induced Graphene Nanocomposites from Polymer Blends

“…The XRD spectra consistently showed a broad peak at ≈17° representing the amorphous phase of the PEI and the PC polymers (Figure d) . Particularly, the ether linkages in the PEI backbone minimize the interchain interactions, and restrict close packing of polymer chains, leading to the formation of amorphous phase . On the other hand, a relatively sharp graphitic (002) peak with a d ‐spacing of ≈3.4 Å is evident at ≈26.4° for the PC10‐LIG nanocomposite and the PEI‐LIG.…”

Effect of sepiolite nanoparticles on the properties of novel poly(sulfone ether imide)

“…It is worthy to mention that the T g values of pristine PSEI and prepared nanocomposites were lower than those of conventional aromatic PIs. This arises from introduction of several flexible ether linkages in the diamine chemical structure which mobilize polymer chains to a considerable extent . T g data obtained from DMTA analysis are listed in Table .…”

“…This arises from introduction of several flexible ether linkages in the diamine chemical structure which mobilize polymer chains to a considerable extent. [27,28] T g data obtained from DMTA analysis are listed in Table 1.…”