Syntheses and properties of polyamides from glucosamine and glucose derivatives

Abstract

Starting from D-glucosamine, the synthesis of various differently modified methyl and benzyl 2,6-diaminosaccharides 11,12,17 and 18 was accomplished. Interfacial and solution polycondensation of those diamino derivates with aromatic and aliphatic acyl chlorides yielded polyamides 34, 35, 36 and 37a-d which were characterized by 'H NMR spectroscopy and their inherent viscosities. The presence of an anomeric benzyl group in 12 did not decrease the reactivity of the 2-amino function. The free hydroxy functions in polyamides 35a-b were acetylated to give polyamides 39ab. Partially blocked polyamides 36a-d had similar properties as unprotected polyamides 34 -35 ad. Under corresponding conditions di-0-acylated diaminosaccharide 18 gave only oligomers. Number-average molecular weights were obtained from gel-permeation chromatography to be 10300 < a,, < 24000 (interfacial polycondensation), corresponding to number-average degrees of polymerization up to P,, = 64, whereas polycondensation in solution afforded only an values between 2000 and 3000. Starting with D-glucose the synthesis of a Cglycosidic diaminosaccharide 28 was developed. This reacted to polyamides 38 ad which showed thermal stability up to 280 "C.

Condensation and Polycondensation of Terephthaldehyde with MethylD-Hexopyranosides

“…[7] Synthetic polymers containing a sugar residue in the main chain were prepared in polycondensations using several combinations of saccharide monomers and dicarboxylic derivatives. [8] Carbohydrates have been derivatized through their hydroxy and amino functions including O-and C-glycosides and poly(vinylsaccharide)s have been obtained as ethers, [9] esters, [10] and amides. [11] A series of polyesters obtained by the condensation of 1,4 : 3,6dianhydro-d-glucidol and 1,4 : 3,6-dianhydro-d-mannitol with several dicarboxylic acid derivatives were synthesized and their biodegradability (in an activated sludge, soil burial and enzymatic degradation) was examined.…”

Green and rapid preparation of thermally stable and highly organosoluble polyamides containing L‐phenylalanine‐9,10‐dihydro‐9,10‐ethanoanthracene‐11,12‐dicarboximido moieties

“…Synthesis of optically active polymers is an important field in polymer science as they have also found potential uses in many fields such as biomedical devices,13, 14 liquid crystals,15 and nonlinear optics 16. An important application of these polymers is chiral recognition, so this ability of chiral polymers has been exploited in various forms of catalytic and separation chemistry 17, 18.…”

Chiral Polymers Containing a Carbohydrate Moiety: Synthesis

“…[4] Synthetic polymers containing a sugar residue in the main chain have been prepared by polycondensation using several combinations of saccharide monomers and dicarboxylic derivatives. [5] Carbohydrates that have been derivatized through their hydroxy and amino functions, including O-and C-glycosides and poly(vinylsaccharide)s, have been obtained as ethers [6] , esters [7] and amides. [8] For example, a series of polyesters obtained by the condensation of 1,4:3,6-dianhydro-D-glucidol and 1,4:3,6-dianhydro-D-mannitol with several dicarboxylic acid derivatives have been synthesized and their biodegradability (in an activated sludge and by soil burial and enzymatic degradation) has been examined.…”