Study of the carbamate/aldehyde reaction, a new pathway towards NIPU materials - Ingénierie des Matériaux Polymères Accéder directement au contenu
Article Dans Une Revue Progress in Organic Coatings Année : 2022

Study of the carbamate/aldehyde reaction, a new pathway towards NIPU materials

Résumé

An innovative alternative to the synthesis of non-isocyanate polyurethanes (NIPUs) thermoset materials was thoroughly investigated. This pathway, involving the reaction between primary carbamate functions and aldehyde functions, was studied using model reactions between ethyl carbamate and different aldehydes that lead to the highlights of the key parameters as well as the first reported proposed mechanism for this reaction. In a second time, polycarbamates synthesized from two different polyols were synthesized via transcarbamoylation before participating in a polycondensation reaction with different monoaldehydes. First a linear NIPU oligomer was synthesized using a dicarbamate derived from ethylene glycol and benzaldehyde. This product was analyzed by NMR spectroscopy and MALDI-TOF mass spectrometry. This oligomer exhibited low molar masses attributed to many secondary termination reactions, mainly due to the presence of acetic anhydride used as solvent in the reaction. Cross-linked NIPU materials were then synthesized without solvent, from the reaction between a tricarbamate derived from trimethylol propane and vanillin, a biobased monoaldehyde, for the first time. The process parameters for the synthesis of these materials were optimized to obtain biobased NIPU thermosetting networks with gel fraction (GF) in dimethylsulfoxide (DMSO) up to 82%, with Tg values ranging between 39°C and 65°C depending on the GF value. This study brings a much needed highlight on the little-known carbamate / aldehyde reaction and demonstrates its potential for the synthesis of novel biobased NIPU thermosetting coatings using a simple monoaldehyde such as vanillin.
Fichier principal
Vignette du fichier
Study of the carbamate-aldehyde reaction, a new pathway towards NIPU materials Gérard 2022.pdf (1.33 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03531119 , version 1 (18-01-2022)

Identifiants

Citer

David Gérard, Françoise Méchin, René Saint-Loup, Etienne Fleury, Jean-Pierre Pascault. Study of the carbamate/aldehyde reaction, a new pathway towards NIPU materials. Progress in Organic Coatings, 2022, 165, pp.106728. ⟨10.1016/j.porgcoat.2022.106728⟩. ⟨hal-03531119⟩
159 Consultations
57 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More