Synthesis of Reactive Amphiphilic Copolymers Based on Oligoglycidol Macromonomers

Abstract

Various linear and branched oligoglycidol macromonomers are prepared using anionic ring opening polymerization of the monomers ethoxyethyl glycidyl ether (EEGE) and glycidol. Starting with 4‐vinyl benzyl alcohol (VBA), allyl glycol or N‐(2‐hydroxyethyl) methacryl amide (HEMAm) oligoglycidol macromomonomers with three to six repeating units are obtained in good yields and characterized with NMR, SEC, DSC and TGA. These macromonomers are versatile tools and can be used as prepolymers for the synthesis of reactive amphiphilic copolymers. The successful conversion of the macromonomers to copolymers via radical polymerization is demonstrated.

Oligoglycidol-Functionalised Styrene Macromolecules as Reactive Surfactants in the Emulsion Polymerisation of Styrene: The Impact of Chain Length and Concentration on Particle Size and Colloidal Stability

“…To study the influence of the oligoglycidol chain length on the surfactant properties of the oligoglycidol-functionalised styrene macromolecule, we synthesized surfmers with three different oligoglycidol chain lengths according to the previously reported procedure [27]. We used vinyl benzyl alcohol (VBA, see Figure S1) and ethoxy ethyl glycidyl ether (EEGE) in ring opening polymerisation to yield poly(ethoxy ethyl glycidyl ether) (PEEGE) 1a-c with 6, 10 and 20 repeating units ( Figure 1).…”

“…One functional moiety that showed great potential in surfmers for the emulsion polymerisation of styrene is oligoglycidol [16]. This functional moiety can be easily modified with a styrene unit for polymerisation [27]. Furthermore, the chain length and number of hydroxyl groups [27] can be varied.…”

“…This functional moiety can be easily modified with a styrene unit for polymerisation [27]. Furthermore, the chain length and number of hydroxyl groups [27] can be varied. It has been shown that oligoglycidol-based surfmers can be used in the emulsion polymerisation of styrene, even below the critical micelle concentration (CMC) [16].…”

Hyperbranched aliphatic polyether polyols

“…The macromonomer strategy has been applied for the synthesis of brush‐type polymers with lin PG side chains, where the methacrylate or styrene functionalized hyperbranched macromonomers were polymerized by free radical147 or atom transfer radical polymerization (ATRP) 148. Möller and coworkers extended this concept in a recent work, where hb PG oligomers with focal acrylate and methacrylate functions were copolymerized with hydrophobic monomers 149. Moreover, Huck and coworkers described the grafting of polyglycerol macromonomers with different topologies from gold surfaces and found a strong dependence of the antifouling properties of the surface, depending on the brush architecture 150…”

Combining oxyanionic polymerization and click-chemistry: a general strategy for the synthesis of polyether polyol macromonomers

“…Polyether-polyols like polyglycerol (PG) show similar properties in terms of biocompatibility, toxicity and antifouling behavior and have therefore been used as very potent multifunctional alternatives to conventional linear PEGs. [3][4][5] This analogy has been transferred to the synthesis of macromonomers both by our group and others, obtaining poly-or oligoglycerol-based macromonomers, [6][7][8] which were shown to be suitable candidates for biomedical applications. 9 The application of click-chemistry 10 in polymer research has clearly led to a huge enhancement of the versatility and synthetic availability of macromolecular architectures.…”