Glycerol-based co-oligomers by free-radical chain transfer polymerization: Towards reactive polymers bearing acetal and/or carbonate groups with enhanced properties

[Display omitted] •The radical polymerization of glycerol based monomers without branching and crosslinking is described.•Carbonate and acetal protective groups are investigated during radical polymerization of glycerol based monomers.•The selective hydrolysis of glycerol protective groups is propos...

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Bibliographic Details
Published in:European polymer journal 2017-10, Vol.95, p.491-502
Main Authors: Pham, Phuoc Dien, Monge, Sophie, Lapinte, Vincent, Raoul, Yann, Robin, Jean Jacques
Format: Article
Language:English
Subjects:
Chain branching
Chain transfer
Chains (polymeric)
Chemical Sciences
Chemical synthesis
Fourier transforms
Gelation
Glycerol
Hydrolysis
NMR
Nuclear magnetic resonance
Oligomers
Polymerization
Polymers
Radical polymerization
Solvents
Spectrum analysis
Studies
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Summary:[Display omitted] •The radical polymerization of glycerol based monomers without branching and crosslinking is described.•Carbonate and acetal protective groups are investigated during radical polymerization of glycerol based monomers.•The selective hydrolysis of glycerol protective groups is proposed.•The solubility of the various oligomers depends largely on the remaining protective group. Oligomers coming from glycerin carbonate acrylate (GCA) and solketal acrylate (SolA) were synthesized in good yields by free-radical chain transfer polymerization using 2-mercaptoethanol (ME) as chain transfer agent. These oligomers were totally soluble in solvents and did not exhibit branching or gelation. The efficiency of the chain transfer polymerization process on these glycerol-based acrylate monomers was demonstrated and reactive cotelomers bearing both acetal and cyclocarbonate groups were obtained. The structure of these oligomers was well-characterized by NMR, SEC, FTIR and MALDI-Tof spectroscopies. The oligo(GC-stat-Sol)s are particularly interesting, notably in terms of reactivity and solubility in various organic solvents and water that can be modulated by varying different SolA/GCA ratios. These results open the way to a widespread valorization of glycerol.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2017.08.014