Synthesis and Characterization of Water Soluble Saccharide Functionalized Polysiloxanes and Their Use as Polymer Surfactants for the Stabilization of Polycaprolactone Nanoparticles

Abstract

Summary: Monosaccharide functionalized polysiloxanes bearing either terminal or pendant mannose moieties have been obtained starting from the allyloxyethyl glycoside and appropriate H‐containing siloxane compounds, via hydrosilylation reactions. The starting modified monosaccharide was reacted as trimethylsilyl protected derivative and a convenient method for deprotection of the hydroxyl groups was found in order to avoid the degradation of the polysiloxane chains. The reaction products were characterized by IR and NMR spectroscopy. The water solubility of these functionalized polysiloxanes was investigated and critical micelle concentration values were found to be in the range 10−4–10−5 M. Some of the water soluble compounds were used as non ionic surfactants for the elaboration of poly(ε‐caprolactone) nanoparticles by nanoprecipitation, and particle sizes of less than 200 nm were observed.

Siloxane surfactants in polymer nanoparticles formulation

“…Nevertheless, it is interesting to note that, in the case of the previously synthesized polymers, 34 this method did not give the expected results, so that we had to use an acidic medium, provided by the gel resin Amberlite IR-120 Plus, in order to cleave the Si-O-C links, while not attacking the Si-O-Si ones. Owing to the large number of protective groups in the cyclosiloxanes, the employment of the same deprotection route seemed appropriate for complete desilylation.…”

One‐Step Method for Synthesis of PDMS‐Based Macroazoinitiators and Block Copolymers from the Initiators

“…1 H NMR Analysis 1 H NMR spectra were recorded on a VANCE DSX-500 spectrometer (Bruker, Germany), and dimethyl sulfoxide-d 6 (DMSO-d 6 ) was used as a solvent for ACPA measurement while chloroform-d 6 (CDCl 3 ) was used for all others.…”

“…[1,2] Consequently, they are viable candidates for applications in thermoplastic elastomers, surfactants, lubricants, water repellents, antifoaming agents, and so on. [3,4] To realize these applications, considerable efforts have been made for the preparation of PDMS-based block copolymers using various approaches, like (1) living anionic polymerization, [5,6] (2) oxyanionic polymerization, [7] (3) living radical polymerization including stable free radical polymerization (SFRP) [8] and atom transfer radical polymerization (ATRP), [9] (4) polycondensation reaction, [10][11][12] and (5) radical polymerization of vinyl monomers with PDMS-based thermally decomposable macroinitiators.…”

Syntheses of Well‐Defined Glyco‐Polyorganosiloxanes by “Click” Chemistry and their Surfactant Properties

“…[3] Since carbohydrates are both renewable and biodegradable raw materials, carbohydrate-modified polysiloxanes have gained increasing attention. So far, numerous examples have been reported where such amphiphilic structures have been used as transdermal penetration enhancers, [4] surfactants, [5][6][7][8][9] and surface modifiers in cosmetics or detergent formulations. [10,11] There exists a commercial product called Wacker-Belsil 1 SPG 128 VP, Well-defined glyco-polyorganosiloxanes were synthesized by the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction (often simply referred to as ''click'' chemistry).…”