Synthesis and characterization of novel polymers derived from gluconolactone

Abstract

A novel synthesis of vinyl monomers derived from D‐gluconolactone, an interesting precursor obtained from D‐glucose, is reported. The derivatization of D‐gluconolactone is carried out by first reacting methacrylic acid with a diamine in water, followed by in situ amidation of the sugar compound. Three monomers containing different lengths of alkylamido groups between vinyl and sugar residues, have thus been obtained and homopolymerized with various free‐radical initiators. The resulting polymers were analysed by viscometry and were found to exhibit polyelectrolyte behaviour. Their structures were confirmed by NMR and consist of a predominantly syndiotactic structure. Copolymerization of the gluconamidoalkyl ammonium methacrylates with other hydrophilic monomers such as methacrylamide and vinylpyrrolidone was also achieved. © 2001 Society of Chemical Industry

Synthesis of Sugar-Based Polypeptides

“…The side NH 3 hydrogen atoms are now visible at 6.95 ppm in CDCl 3 /TFA solution. 13 C-NMR analysis also confirmed complete deprotection with the presence of only one carbonyl signal centered at 174.5 ppm attributable to the peptide carbon (Fig. 2).…”

“…Our group reported previously the synthesis of polyvinylics containing gluconoyl moieties as side-groups [13]. The main objective of that work was to impart hydrophilicity to the polyvinylics.…”

“…The polymer was isolated by precipitation in water and dried under vacuum at room temperature. The polymer was characterized by 1 H, 13 C-NMR and SEC.…”

“…The reaction was left to proceed at ambient temperature till all monomers were consumed. The co-polypeptide was isolated by precipitation in water, dried under vacuum and characterized by 1 H, 13 C-NMR and SEC.…”

Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces

“…In this way, the exploration of novel fluoroalkyl end-capped oligomers containing numerous hydroxyl segments is of particular interest, from the developmental viewpoints of new fluorinated functional materials. In a variety of hydroxylated polymers, much attention has been focused on the synthetic sugar-containing polymers (glycopolymers), which possess the pendent gluconic residues (pentaol units), owing to their role as biomimetic analogues and their applications in biomedical and technological fields such as paints and cosmetics [10][11][12][13][14][15][16][17][18][19]. In fact, poly(allylamine) can react with gluconolactone in water to provide the gluconamide-substituted polymers, successively affording the hydrogel through the interaction of the corresponding polymers with borax [20].…”