Synthesis and characterization of new aromatic sulfone ether polyamides containing pendant pentadecyl groups

Abstract

A series of new polyamides and copolyamides containing aromatic sulfone ether linkages was synthesized from 4,4′‐[sulfonyl‐bis(4,1‐phenyleneoxy‐3‐pentadecyl)]bisphenylamine (SPPBA) and isophthaloyl chloride (IPC), terephthaloyl chloride (TPC), bis(4‐chlorocarbonylphenyl)dimethylsilane (DMSC) and bis(4‐chlorocarbonylphenyl)diphenylsilane (DPSC) by a low‐temperature inter‐facial polymerization technique. SPPBA was prepared from 4,4′‐dichlorodiphenyl sulfone and 4‐amino‐3‐pentadecyl phenol derived from cashew‐nut shell liquid and was characterized by spectral methods and elemental analysis, whereas the polyamides were characterized by solution viscosity, IR spectroscopy, thermogravimetric analysis, X‐ray diffraction and solubility. These polyamides showed enhanced solubility in organic solvents and no weight loss below 405°C in nitrogen. The effect of pendant penladecyl substituents and silicon in the main chain of polyamides on the properties of these polymers was studied by comparing their properties with those of unsubstituted polyamides prepared from 4,4′‐[sulfonylbis(4,1 ‐phenyleneoxy)] bisphenylamine.

Functionalization of cardanol: towards biobased polymers and additives

“…were synthesized starting from cardanol (Scheme 18). 102,126,[200][201][202][203][204][205][206][207][208][209][210][211][212][213][214][215][216] These difunctional monomers were utilized for the synthesis of a variety of high performance polymers such as aromatic polyimides, polyamides, poly(azomethine)s, poly-(amideimide)s, poly(esterimide)s, polyesters, polyhydrazides, polyoxadiazoles, etc. The effects of incorporation of pendent pentadecyl chains on solubility and thermal properties of the polymers were evaluated.…”

Aromatic Polyesters Containing Ether and a Kinked Aromatic Amide Structure in the Main Chain: Synthesis and Characterisation

“…However, wholly polyarylates are insoluble and have high glass transition or melting temperatures and are hence difficult to process. The ordering and structural variations of polymer backbones decide the final properties of the polymer [4,5]. Earlier investigations showed that modified cardo groups [6,7] and pendant moieties [8][9][10][11][12] produced amorphous polyesters that dissolved in organic solvents.…”

“…Earlier investigations showed that modified cardo groups [6,7] and pendant moieties [8][9][10][11][12] produced amorphous polyesters that dissolved in organic solvents. Polyesters derived from CNSLbased monomers showed relatively lower glass transition temperatures in addition to the enhanced solubility of these polyesters in some organic solvents, probably due to the plasticising effect of the pendant long pentadecyl alkyl groups [5,9]. Good melt-processability of the polymers required lower glass transition temperatures so that processing could be performed at relatively lower temperatures.…”

Bio-based Aromatic Amines from Lignin-Derived Monomers

“…Remarkably, while aliphatic amines have been extensively studied, only a few examples are hitherto reported for aromatic amine synthesis. These are all based on cardanol, extracted from cashew nut shell liquid, and involve S E Ar reactions. − Cardanol derivatives are nitrated with nitric acid or undergo diazo coupling with the diazonium salt of sulfanilic acid. Reduction toward amine is performed in the presence of a Pd/C catalyst with hydrazine for the nitro and with sodium dithionite for the diazo group.…”