Functionalization of Poly(ethylene terephthalate) Fibers by Photografting of a Carbohydrate Derivatized with a Phenyl Azide Group

Abstract

Grafting of a new carbohydrate UV-reactive molecule, an azidophenyl lactamine (AzPhLac), was achieved on fibers of three different diameters: 12, 18, and 32 microm. Adsorption of AzPhLac on fibers was obtained by using the dip-coating method in solution. The effect of the solution concentration on surface density and yield of grafted AzPhLac was investigated. Surface densities in the range 3-67 nmol/cm2 were obtained without marked difference related to the diameter of the fiber. Quantitative grafting was obtained with a surface of fiber of 1 cm2 and the lowest concentration (0.5 mM) of AzPhLac solution. The surface density and grafting yield decreased with the available surface of the fibers. This phenomenon could be attributed to a masking core-shell effect with outer fibers in the shell preventing the UV grafting of the fibers located in the core of the fibers' bundles. Scanning electron (SEM) and atomic force (AFM) microscopic observations suggested that homogeneous grafting might be obtained.

Synthesis of glycopolymers and their multivalent recognitions with lectins

“…Examples include the chemical modification of poly(vinyl alcohol) (PVA) by glycosidation with triacetylated sugar oxazoline, 137 the reaction between poly[(9,9-bis-(6 0 -bromohexyl)-2,7-fluorenylene)-alt-1,4-phenylene] and thio-sugar, 138 the use of carbohydrates bearing aldehyde groups which react efficiently with polymers with pendant amino residues 139 and the functionalization of poly(ethylene terephthalate) (PET) fibres with glycosyl azides. 140 None of these polymers were however tested for their bioactivity.…”

Synthesis and Application of New Photocrosslinkers for Poly(ethylene glycol)

“…The bis-arylazides 5-6 showed globally the same behaviour and enabled the photocrosslinking of PEG in aqueous acetonitrile solution, but not in bulk owing again to self-coupling of the photolinkers, as seen by other groups. [25] Best results were found by using 6a (i.e. two 4-azido-2,3,5,6tetrafluorobenzoyl motifs connected with a tetraethyleneglycol spacer via amide bonds), allowing the production of soluble crosslinked PEG of ,300 kDa, together with highly branched insoluble PEG that we were not able to characterize further.…”

Carbohydrate, Biomaterials, and Tissue Engineering Applications

“…Although the precise mechanism of surface modification is not fully understood, this method has been demonstrated to be very effective for a wide range of surfaces. This approach has been used recently to covalently link carbohydrates to polyethylene terephthalate (PET) fibers by Renaudie et al [83], for example, by incorporating a sialyl-Lewis X saccharide, as it is known to interact specifically with L-selectin [84]. Thus, a new method for grafting a carbohydrate UV-reactive molecule, an azidophenyl lactamine (AzPhLac), Fig.…”