Composite Polymer Materials Consisting of Nanofilms Formed by Click Reaction between Polymers at an Oil–Water Interface

Abstract

New polymer materials, including thin films, soft gels, and hollow capsules, consisting of composite polymer nanofilms were prepared by the Cu(I)-catalyzed Huisgen click reaction between lipophilic polymers or between lipophilic and hydrophilic polymers. Because the lipophilic polymer, or hydrophilic polymer and copper catalyst were present in the oil or aqueous phase, respectively, the crosslinking reaction proceeded only at the phase interface. The combination of lipophilic and hydrophilic polymers produced “Janus” nanofilms with both hydrophilic and lipophilic surfaces.

Interfacial click chemistry for improving both dextran shell density and stability of biocompatible nanocapsules

“…22 Many excellent reviews reported on different techniques for NCs preparation [4,5,16,17]. 23 These methods can be classified into three main groups: (i) deposition (or precipitation) of 24 preformed polymer on a nano-emulsion template (for example layer-by-layer deposition of 25 opposite charged polyelectrolytes [18]) (ii) phase segregation between the polymer 26 constituting NCs shell and the liquid core leading to polymer precipitation at the interface 27 during the NPs production (for example by emulsion-/evaporation process [19] or by 28 miniemulsion polymerization [20]) and finally, (iii) polymerization at water/droplet interface 29 [21]. In the last case, polycondensation between two monomers (one being in continuous 30 phase, the other in dispersed phase) is the most common [22].…”

“…Despite its 38 advantages, the use of CuAAC for polymer coupling at liquid/liquid interface, i.e. each phase 39 containing one of the two correctly functionalized polymers, has only been reported scarcely 40 in the literature [13,[25][26][27][28]. This certainly originated from difficulties to obtain sufficiently 41 high coupling efficiency between polymers related to limited accessibility of functional 42 groups at the interface.…”

Investigation of Click Reaction at an Oil-Water Interface Using Hydrophobic and Hydrophilic Polymers

“…The procedure for synthesis of copolymer poly(NaSS-co-PgA) was described in our previous paper 10 . Hydrophilic copolymer bearing alkyne units, (sodium styrene sulfonate (NaSS) and propargyl acrylate (PgA 11 )) was prepared by copolymerization in DMSO using AIBN initiator.…”

“…Purification was conducted by dialyzing entirely against deionized water using dialysis bag (3,500 MW cutoff). The molar ratio of PgA in the copolymer was determined 9.1 mol% through 1 H NMR spectral analysis reported in our previous article 10 . The most popular and widely used copper-catalyzed azide-alkyne cycloaddition is also known as the Huisgen click reaction 12 .…”

“…Rotello and coworkers 6 International Letters of Chemistry, Physics This work was motivated by recent reports demonstrating methods for the fabrication of nanofilms, hollow microcapsules and gel. For example, in our recent article 10 we have reported a simple click reaction between polymers, poly(2-hydroxy-3-azidopropyl methacrylate) (poly(HAzPMA)), poly(styrene-co-2-azidethyl acrylate) poly(Sty-co-AzA), poly(propargyl methacrylate) (poly(PgMA)) and poly(sodium styrene sulfonate-co-propargyl acrylate) (poly(NaSS-co-PgA)), at macroscopic oil-water interfaces in biphasic phase solutions, oil-in-water (O/W) or water-in-oil (W/O) droplets, and use mechanical emulsions to construct new polymer materials based on nanofilms consisting of crosslinked polymers.…”