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…
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References
SHOWING 1-10 OF 95 REFERENCES
Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors
- Chemistry
- 2014
(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…
Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s
- Chemistry, Materials Science
- 2014
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…
Access to nonisocyanate poly(thio)urethanes: A comparative study
- Chemistry
- 2013
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…
Rational investigations in the ring opening of cyclic carbonates by amines
- Chemistry
- 2014
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…
Addition of five‐membered cyclic carbonate with amine and its application to polymer synthesis
- Chemistry
- 2000
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…
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
- Chemistry
- 2001
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…
Optically active poly(hydroxyurethane)s derived from cyclic carbonate andL-lysine derivatives
- Chemistry
- 1996
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…
Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis
- Chemistry
- 2010
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…