Search results for "Glycidol"
showing 10 items of 36 documents
Catechol Acetonide Glycidyl Ether (CAGE): A Functional Epoxide Monomer for Linear and Hyperbranched Multi-Catechol Functional Polyether Architectures
2016
A protected catechol-containing epoxide monomer, catechol acetonide glycidyl ether (CAGE), is introduced. CAGE is conveniently obtained in three steps and enables the incorporation of surface-active catechol moieties into a broad variety of hydrophilic and biocompatible polyether architectures by copolymerization. Via acidic cleavage of the acetal protecting groups, the polymer-attached catechol functionalities are liberated and available for surface attachment or metal complexation. CAGE has been copolymerized with ethylene oxide and glycidol to obtain both linear poly(ethylene glycol) and hyperbranched polyglycerol copolymers, respectively, with multiple surface-adhesive catechol moieties…
The “Needle in the Haystack” Makes the Difference: Linear and Hyperbranched Polyglycerols with a Single Catechol Moiety for Metal Oxide Nanoparticle …
2014
Multifunctional linear (CA-linPG) and hyperbranched polyglycerols (CA-hbPG) bearing a single catechol unit were synthesized by use of an acetonide-protected catechol initiator for the anionic polymerization of ethoxyethyl glycidyl ether (EEGE) and glycidol, respectively. A key feature for the synthesis of the hyperbranched structures was a selective, partial acetal deprotection step. The single catechol unit among a large number of aliphatic 1,2- and 1,3-diol moieties (i.e., the “needle in the haystack”) in both linear and hyperbranched polyglycerols permits dispersion of transition metal oxide nanoparticles in brine, as demonstrated for manganese oxide (MnO) nanoparticles. Molecular weight…
From an epoxide monomer toolkit to functional PEG copolymers with adjustable LCST behavior.
2011
The lower critical solution temperature (LCST) behavior of novel poly(ethylene glycol) (PEG)-based copolymers bearing multiple functional groups, obtained by anionic ring-opening (co)polymerization (AROP), has been investigated. Variable comonomer ratios of ethylene oxide (EO) and the corresponding oxiranes isopropylidene glyceryl glycidyl ether (IGG), ethoxyl vinyl glycidyl ether (EVGE), allyl glycidyl ether (AGE), or N,N-dibenzyl amino glycidyl (DBAG), particularly designed to implement functional groups at the PEG backbone, were found to influence the LCST behavior. Sharp transitions from translucent to opaque solutions, comparable to other well-established stimuli-responsive polymers, w…
Amino Functional Poly(ethylene glycol) Copolymers via Protected Amino Glycidol
2010
The synthesis of poly(ethylene glycol) (PEG) copolymers with multiple amino functionalities within the chain is described, relying on an epoxide comonomer bearing a protected amino group. N,N-dibenzyl amino glycidol (DBAG) and ethylene oxide (EO) were copolymerized via anionic polymerization, leading to well-defined polymers with varied comonomer content and low polydispersities (Mw/Mn in the range of 1.1 to 1.2). Subsequent hydrogenolysis with Pearlman’s catalyst afforded poly(ethylene glycol-co-amino glycerol)s (PEG-co-PAG) with a precisely adjusted number of randomly incorporated amino groups in the range of 2−15%. For the first time, the kinetics of an EO copolymerizations have has been…
“Functional Poly(ethylene glycol)”: PEG-Based Random Copolymers with 1,2-Diol Side Chains and Terminal Amino Functionality
2010
A series of poly(ethylene glycol-co-isopropylidene glyceryl glycidyl ether) (P(EO-co-IGG)) random copolymers with different fractions of 1,2-isopropylidene glyceryl glycidyl ether (IGG) units was synthesized. After acidic hydrolysis a new type of "functional PEGs", namely poly(ethylene glycol-co-glyceryl glycerol) (P(EO-co-GG)) was obtained. Using an initiator that releases a terminal amino moiety after deprotection, functional end groups with orthogonal reactivity to the in-chain groups were obtained. All polymers showed narrow molecular weight distributions (1.07-1.19), and control of the molecular weights was achieved in the range 5000-30 000 g/mol. Random incorporation of both comonomer…
Hyperbranched Polyglycerols: From the Controlled Synthesis of Biocompatible Polyether Polyols to Multipurpose Applications
2009
Dendritic macromolecules with random branch-on-branch topology, termed hyperbranched polymers in the late 1980s, have a decided advantage over symmetrical dendrimers by virtue of typically being accessible in a one-step synthesis. Saving this synthetic effort once had an unfortunate consequence, though: hyperbranching polymerization used to result in a broad distribution of molecular weights (that is, very high polydispersities, often M(w)/M(n)5). By contrast, a typical dendrimer synthesis yields a single molecule (in other words, M(w)/M(n) = 1.0), albeit by a labor-intensive, multistep process. But 10 years ago, Sunder and colleagues reported the controlled synthesis of well-defined hyperb…
Synthèse et formulation de résines photopolymérisables issues de la biomasse : application pour l'impression Braille
2014
The work of the PhD deals with the synthesis of polymerizable monomers derived from biomass, the study of their photopolymerization and the characterization of the resulting materials. The formulated monomers were tested in a printing method of Braille characters.The monomers were prepared in a two-steps reaction that is simple, economic and environmentally friendly. The first step comprised a reaction between glycerol derivatives (glycerol carbonate or glycidol) and fatty acids. In the second step, the obtained [alpha]-monoglycerides were functionalized to obtain photopolymerizable monomers. The different obtained monomers that bear (meth)acrylate and/or epoxy groups were photopolymerized …
Beyond Poly(ethylene glycol): Linear Polyglycerol as a Multifunctional Polyether for Biomedical and Pharmaceutical Applications
2014
Polyglycerols (sometimes also called "polyglycidols") represent a class of highly biocompatible and multihydroxy-functional polymers that may be considered as a multifunctional analogue of poly(ethylene glycol) (PEG). Various architectures based on a polyglycerol scaffold are feasible depending on the monomer employed. While polymerization of glycidol leads to hyperbranched polyglycerols, the precisely defined linear analogue is obtained by using suitably protected glycidol as a monomer, followed by removal of the protective group in a postpolymerization step. This review summarizes the properties and synthetic approaches toward linear polyglycerols (linPG), which are at present mainly base…
Efficient microwave-assisted synthesis of glycerol monodecanoate
2017
International audience; Solvent-free microwave-assisted synthesis was carried out to prepare 2,3-dihydroxypropyl decanoate, by esterification of decanoic acid in the presence of two distinct glycerol derivatives, glycidol, and glycerol carbonate, respectively. The process described is based on microwaves heating source with electrical power in the range of 200–400 W, involving stoichiometric proportions of decanoic acid and glycerol derivatives, and using catalytic amounts of TBAI used as organocatalyst. Conversion and selectivity rates of esterification reactions were monitored by 1H and 13C{1H} NMR spectroscopy. The predominantly formed ester, 2,3-dihydroxypropyl decanoate was fully chara…
Undecylenic acid: A tunable bio-based synthon for materials applications
2016
International audience; An undecylenic acid-based monoglyceride prepared from glycidol and undecylenic acid is used as suitable and tunable synthon for polymerization applications. Epoxidation and acrylation reactions lead to photopolymerizable monomers while transesterification with dimethyl carbonate, metathesis and aminolysis reactions provide access to polyhydroxyurethane-based materials. The successive intermediates were synthesized according to a green chemistry approach implicating solvent-less and catalyzed reactions, and were at each step fully characterized by infrared, 1H and 13C{1H} NMR spectroscopy, elemental analysis and mass spectrometry. Analyses of the resulting polymer mat…