Synthesis of chiral and racemic functional polymers from glycidol and thioglycidol

Taton, Daniel; Borgne, Alain Le; Sépulchre, Maurice; Spassky, Nicolas

doi:10.1002/macp.1994.021950111

Cited by 152 publications

(164 citation statements)

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“…[86] Linear PG has been obtained from the polymerization of protected glycidols and the polymerization of 3-hydroxyoxetane. [87][88][89] Dworak and coworkers [90] carried out cationic polymerization of glycidol under the action of Lewis acids (BF 3 OEt 2 , SnCl 4 ) and protonic acids (CF 3 COOH, CF 3 SO 3 H) and polymers with number-average molecular weights varying from 2500 to 6000 g mol À1 were obtained. Structural and mechanistic details of such polymerization process have been reported and it was found that the structure of the polymers was related to the contribution of activated monomer mechanism in chain growth.…”

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confidence: 99%

Dendritic Polyglycerols for Biomedical Applications

et al. 2009

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The application of nanotechnology in medicine and pharmaceuticals is a rapidly advancing field that is quickly gaining acceptance and recognition as an independent area of research called "nanomedicine". Urgent needs in this field, however, are biocompatible and bioactive materials for antifouling surfaces and nanoparticles for drug delivery. Therefore, extensive attention has been given to the design and development of new macromolecular structures. Among the various polymeric architectures, dendritic ("treelike") polymers have experienced an exponential development due to their highly branched, multifunctional, and well-defined structures. This Review describes the diverse syntheses and biomedical applications of dendritic polyglycerols (PGs). These polymers exhibit good chemical stability and inertness under biological conditions and are highly biocompatible. Oligoglycerols and their fatty acid esters are FDA-approved and are already being used in a variety of consumer applications, e.g., cosmetics and toiletries, food industries, cleaning and softening agents, pharmaceuticals, polymers and polymer additives, printing photographing materials, and electronics. Herein, we present the current status of dendritic PGs as functional dendritic architectures with particular focus on their application in nanomedicine, in drug, dye, and gene delivery, as well as in regenerative medicine in the form of non-fouling surfaces and matrix materials.

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confidence: 99%

Dendritic Polyglycerols for Biomedical Applications

et al. 2009

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“…[14] Control over the degree of polymerization and narrow molecular weight distributions was guaranteed by the sequential living anionic ring-opening polymerization of protected glycidyl ethers (Scheme 2). [17][18][19] All polymerizations were initiated with the cesium salt of 3-phenylpropanol and…”

Section: Synthesis Of Amphiphilic Polyglycerol Block Copolymersmentioning

confidence: 99%

“…Deprotection of the acetal block leads to amphiphilic block copolymers. Insets: SEC elugrams, of P2 (PG 17 -b-PAGE 17 ) and P5 (PG 28 -b-PtBuGE 31 , DMF, 333 K, RI detection, 1 mL min −1 ) of first block (P2-1, P5-1), protected block copolymers (P2-2, P5-2), and deprotected block copolymers (P2, P5) (all SEC traces were normalized).…”

Section: Synthesis Of Amphiphilic Polyglycerol Block Copolymersmentioning

confidence: 99%

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Wald

Simon

Dietz

et al. 2017

Macromolecular Bioscience

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studied as promising surfactants for emulsions. [10] Furthermore, vinyl-terminated polyglycerols were used as surfmers to synthesize stable polystyrene (PS) microspheres for medical diagnostics for possible postfunctionalization with proteins. [11,12] Hyperbranched and linear surfmers based on polyglycerols were additionally used to generate stable PS nanoparticles. [13] However, for the miniemulsion approach only less multifunctional PG-based surfactants or surfmers are known.Here, we use the versatility of the anionic polymerization of glycidyl ethers to prepare a series of multifunctional (additional OH-groups or polymerizable CC-groups) surfactants with adjustable hydrophiliclipophilic balance (HLB) that allows the stabilization of direct (oil-in-water) or inverse (water-in-oil) (mini)emulsions or can be used simultaneously for both systems.Two known orthogonal protection strategies, reported by Möller and coworkers, [14] were used to synthesize linear completely poly glycerol-based block copolymers as surfactants or surfmers for direct, inverse, or both types of miniemulsions (Scheme 1). The orthogonal-protected block copolymers were generated by anionic ring-opening polymerization in bulk using ethoxyethyl glycidyl ether (EEGE) and allyl glycidyl ether (AGE) or tert-butyl glycidyl ether (tBuGE) with defined block length ratios to tune their HLB. After acidic hydrolysis of the acetal groups, the water-soluble allyl-functionalized PG block copolymers were established as surfmers in the radical miniemulsion poly merization of styrene to generate polystyrene nanoparticles with decreased protein adsorption behavior due to incorporated PG surfactants (Scheme 1). In addition, oil-soluble allyl-functionalized block copolymers were introduced as surfmers to produce polyurea/urethane nanocapsules by interfacial polyaddition reactions of hydroxyethyl starch (HES) with toluene diisocyanate (TDI) (Scheme 1). [15] Furthermore, the allyl-protection groups on the polyurethane nanocarrier surface were utilized for surface functionalization by thiol-ene addition in water. For this purpose, the nanocarriers were transferred into water including a tert-butyl-protected poly glycerol block copoly mer. The tert-butyl-protected polyglycerol block copolymers were applied as surfactant to generate polystyrene nanoparticles in direct miniemulsions for comparison with the allyl-protected surfmer and in inverse miniemulsions to produce stable poly(hydroxyethyl methacrylate) (PHEMA)

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“…Obwohl bereits Mitte der 90er Jahre beschrieben, [57,58] [59][60][61] und Anwendungen in der kombinatorischen Therapie mçglich. [8] Multifunktionelle PEGCopolymere sind jedoch nicht auf pharmazeutische und biomedizinische Anwendungen beschränkt, sondern beispielsweise für das Gebiet der Katalyse ebenfalls sehr interessant.…”

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Multifunktionelle Poly(ethylenglycole)

et al. 2011

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Maßgeschneiderte makromolekulare Strukturen stellen auf dem sich stetig entwickelnden Feld der Polymertherapeutika die Schlüsselkomponente dar, um das Potential bioaktiver Konjugate auszuschöpfen. Die jüngsten Entwicklungen auf dem Gebiet der Wirkstoffkonjugate zur Krebsbehandlung zeigen, dass multifunktionelle Polymere als Wirkstoffträger immer bedeutender werden. Die Anwendung des vermeintlich am besten geeigneten Polymers, Poly(ethylenglycol) (PEG), ist hier jedoch durch die limitierte Zahl funktioneller Gruppen eingeschränkt. Als Resultat ziehen multifunktionelle Copolymere basierend auf Ethylenoxid (EO) und einem entsprechenden Epoxid als Comonomer (mf‐PEGs) zunehmend Aufmerksamkeit auf sich. Wohldefiniert dargestellt durch lebende anionische Polymerisation in Kombination mit modernen Charakterisierungsmethoden – beispielsweise Messungen der Polymerisationskinetik über 1H‐NMR‐Spektroskopie in Echtzeit –, repräsentiert diese aufkommende Klasse an Polymeren eine leistungsstarke Plattform zur Synthese von Bio‐ und Wirkstoffkonjugaten.

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Synthesis of chiral and racemic functional polymers from glycidol and thioglycidol

Cited by 152 publications

References 9 publications

Dendritic Polyglycerols for Biomedical Applications

Dendritic Polyglycerols for Biomedical Applications

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

Multifunktionelle Poly(ethylenglycole)

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