Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis

@article{Lamarzelle2016ActivatedLC,
  title={Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis},
  author={Océane Lamarzelle and P. Durand and Anne-Laure Wirotius and Guillaume Chollet and {\'E}tienne Grau and Henri Cramail},
  journal={Polymer Chemistry},
  year={2016},
  volume={7},
  pages={1439-1451}
}
Activated 5-membered cyclic carbonates were prepared from glycerol and fatty acid derivatives. Ester and ether moieties were introduced in the β position to the cyclic carbonate, in order to enhance its reactivity towards amines. 1H NMR kinetic investigation of the aminolysis of these cyclic carbonates demonstrated a higher reactivity compared to the one of alkyl substituted cyclic carbonates. In the case of ester-activated carbonates, a reactivity similar to the one of 6-membered ring cyclic… Expand
View via Publisher
hal.archives-ouvertes.fr
67 Citations
Background Citations
3
Methods Citations
2

Figures from this paper

67 Citations

Citation Type

Citation Type

A study of cyclic carbonate aminolysis at room temperature: effect of cyclic carbonate structures and solvents on polyhydroxyurethane synthesis
In recent years, intensive research and development have been carried out for the synthesis of isocyanate free polyurethanes from the reaction between five-membered cyclic carbonates and amines to… Expand
Enhanced aminolysis of cyclic carbonates by β-hydroxylamines for the production of fully biobased polyhydroxyurethanes
The aminolysis of five-membered cyclic carbonates, which results in polyhydroxyurethanes (PHUs), is one of the most promising synthetic pathways to achieve isocyanate-free polyurethanes (NIPUs), one… Expand
A thioglycerol route to bio-based bis-cyclic carbonates: poly(hydroxyurethane) preparation and post-functionalization
The present work is dedicated to the design of novel sulfur-substituted cyclic carbonates from thioglycerol, fatty acids and sugar derivatives. In this methodology, a sulfur atom is inserted in the β… Expand
Synthesis of High-Molecular-Weight Multifunctional Glycerol Polyhydroxyurethanes PHUs
Glycerol carbonate acrylate is a 5-membered cyclic carbonate synthesized from glycerol that is used as a chemical coupling agent and has proven highly suitable for use in the synthesis of… Expand
Upgrading castor oil: From heptanal to non-isocyanate poly(amide-hydroxyurethane)s
Abstract Intensive research has recently been carried out to synthesize non-isocyanate polyurethanes (NIPUs) from five-membered cyclic carbonates and amines as a sustainable route to industrial… Expand
Reactive jojoba and castor oils-based cyclic carbonates for biobased polyhydroxyurethanes
Abstract Syntheses of novel biobased PolyHydroxyUrethane (PHU) have been performed from Jojoba and castor oil. Cyclic carbonate monomers with various functionality were synthesized from both jojoba… Expand
Room temperature synthesis of non-isocyanate polyurethanes (NIPUs) using highly reactive N-substituted 8-membered cyclic carbonates
There is a growing interest to develop green synthetic pathways towards industrially relevant polymers such as polyurethanes without the use of toxic and dangerous isocyanate monomers. The most… Expand
Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock
Glycerol serves as the exclusive bio feedstock for the preparation of high purity sorbitol tricarbonate (STC) as new intermediate for poly(carbohydrate–urethane) thermosets and 100% bio-based… Expand
Synthesis of fatty acid-based non-isocyanate polyurethanes, NIPUs, in bulk and mini-emulsion
The synthesis of fatty acid-based poly(hydroxy urethane)s, PHUs, was investigated. Bulk polymerization of fatty acid-based bis-carbonates with fatty acid diamine, Priamine® 1075, was first studied,… Expand
Synthesis and characterization of elastomeric, biobased, nonisocyanate polyurethane from natural rubber
Linear and crosslinked polyhydroxyurethanes (PHUs) based on natural rubber (NR) were synthesized by a polyaddition reaction without a solvent or catalyst to exploit the reactivity of diamines or… Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 95 REFERENCES
Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors
(Bis) 6-membered cyclic carbonates were prepared from methyl 10-undecenoate, which is produced from ricinoleic acid, a main constituent of castor oil. Kinetic studies on these new fatty acid-based… Expand
Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s
Fatty acid-based bis-cyclic 5-membered carbonates containing amide linkages were prepared from methyl 10-undecenoate. The reaction in bulk of these bio-based carbonates with a series of di-amines led… Expand
Access to nonisocyanate poly(thio)urethanes: A comparative study
This article describes the synthesis of new cyclic compounds able to react with amines to get nonisocyanate polyurethanes (NIPUs). The contribution of the most studied five-membered cyclic carbonate… Expand
Rational investigations in the ring opening of cyclic carbonates by amines
Non-isocyanate polyurethanes (NIPUs) constitute a promising alternative for more classical polyurethanes (PUs) as they may display mechanical properties that can match those of PUs and their… Expand
Poly(hydroxy urethane)s based on renewable diglycerol dicarbonate
Abstract In this paper, we present a series of amorphous non-isocyanate poly(hydroxy urethane)s (PHU) synthesized from diglycerol dicarbonate in bulk conditions at mild temperatures, without using a… Expand
Addition of five‐membered cyclic carbonate with amine and its application to polymer synthesis
A bifunctional five-membered cyclic carbonate was synthesized from carbon dioxide and diglycidyl terephthalate, and its polyaddition with alkyl diamines were carried out in DMF at room temperature to… Expand
Model reaction for the synthesis of polyhydroxyurethanes from cyclic carbonates with amines: Substituent effect on the reactivity and selectivity of ring‐opening direction in the reaction of five‐membered cyclic carbonates with amine
This article focuses on the substituent effect on the reactivity and selectivity of the ring-opening direction in the reaction of five-membered cyclic carbonates with n-hexylamine. The reactivity of… Expand
Optically active poly(hydroxyurethane)s derived from cyclic carbonate andL-lysine derivatives
The polyaddition of L-lysine hydrochloride and bifunctional five-membered cyclic carbonate 1 was carried out in DMAc in the presence of 1 equiv of DBU or 2 equiv of sodium hydride for 24 h to afford… Expand
Branched cationic polyurethane prepared by polyaddition of chloromethylated five‐membered cyclic carbonate and diethylenetriamine in molten salts
Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis
Novel linear polyurethanes were synthesized by bulk polyaddition of diamines with two vegetable-based biscarbonates produced from oleic acid methyl ester. Internal carbonated fatty acid diester… Expand
...
1
2
3
4
5
...