Isocyanate-Free Polyurethanes by Coreaction of Condensed Tannins with Aminated Tannins

Published on Jan 7, 2017in Journal of Renewable Materials1.67
路 DOI :10.7569/JRM.2016.634116
F. Al-Marzouki7
Estimated H-index: 7
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Abstract
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20184.33Polymers
3 Authors (Xuedong Xi, ..., Luc Delmotte)
References17
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#2Antonio Pizzi (University of Lorraine)H-Index: 80
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Mixed phenolic-polyurethane-type rigid foams were developed using tannin-furfuryl alcohol natural materials co-reacted with polymeric isocyanate in the proportions imposed by the limitations inherent to continuous industrial plants for polyurethane foams. A variety of different copolymerization oligomers formed. Urethanes appeared to have been formed with two flavonoid tannin sites, mainly at the flavonoid hydroxyl group at C3, but also, although less, on the phenolic hydroxyl groups of the flav...
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#1Marion Th茅bault (University of Lorraine)H-Index: 8
#2Antonio Pizzi (University of Lorraine)H-Index: 80
Last. Luc Delmotte (CNRS: Centre national de la recherche scientifique)H-Index: 29
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Abstract Hydrolysable chestnut tannins, which contain several hydroxyl groups, were reacted with dimethyl carbonate, and then with hexamethylenediamine. The dried product was analyzed in MALDI-TOF, 13 C NMR and FTIR spectrometry. The spectra revealed the presence of urethane functions and their yield was relatively high. This synthesis of polyurethanes is interesting because it does not depend on using isocyanates as reactants while instead utilizing a natural material, hydrolysable chestnut tan...
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#1M.C. BassoH-Index: 16
#2Samuele GiovandoH-Index: 10
Last. Alain Celzard (University of Lorraine)H-Index: 68
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Open cell foams obtained by the simultaneous coreaction of condensed flavonoid tannins with an alkoxylated fatty amine and polymeric diphenylmethane isocyanate yielded highly flexible/elastic polyurethane foams. Copolymerized amine/isocyanate/tannin oligomers were identified by 13 C NMR and MALDI-TOF spectroscopy. In general, between 30% and 50% of natural tannins is added to the components used to obtain polymerisation of the polyurethane. The characteristic of these new, partially biosourced p...
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The catalytic chemical fixation of carbon dioxide by carbonation of oxiranes, oxetanes, and polyols represents a very versatile green chemistry route to environmentally benign di- and polyfunctional cyclic carbonates as intermediates for the formation of non-isocyanate poly颅urethane (NIPU). Two synthetic pathways lead to NIPU thermoplastics and thermosets: i) polycondensation of diacarbamates or acyclic dicarbonates with diols or diamines, respectively, and ii) polyaddition by ring-opening polym...
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#1Vincent Besse (ENSCM: 脡cole nationale sup茅rieure de chimie de Montpellier)H-Index: 11
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Great attention has always been paid to monomers bearing at least two reactive groups, one for copolymerization and one for further reaction, in particular, for cross-linking. Such reactive groups should be reactive enough for crosslinking but should not prevent any copolymerization of monomers. Cyclic carbonate groups are currently gaining increasing attention both from academic and industrial communities. Indeed, these functions allow better control in terms of spontaneous crosslinking reactio...
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#1Bassam Nohra (University of Toulouse)H-Index: 5
#2Laure Candy (University of Toulouse)H-Index: 11
Last. Z茅phirin Mouloungui (University of Toulouse)H-Index: 28
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From a green and sustainable chemistry standpoint, the current challenge in the polyurethane鈥檚 industry is to switch from petrobased polyurethanes (PUs) to biobased polyhydroxyurethanes (PHUs). This review describes the main alternative strategies being developed with a focus on PHUs from vegetable oils and derivatives. The substitution of petrobased polyols by natural oil based polyols was the first route to biobased PUs to be developed. The second strategy involves synthesis without the need o...
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#1Ying Peng (SJTU: Shanghai Jiao Tong University)H-Index: 3
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A novel adhering polyurethane (PU), based on hydrolysable tannins that contain a number of active sites, was successfully synthesized and characterized. The active sites were catechol groups in the hydrolysable tannins, which were used as a substitute for dopamine. This efficient, universal, and low cost coating based on hydrolysable tannins was cured by adding FeCl3, and was evaluated by nuclear magnetic resonance (1H-NMR), Fourier transform infrared (FTIR), differential scanning calorimetry (D...
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#1Flavia Lega Braghiroli (University of Lorraine)H-Index: 15
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Abstract Reaction of condensed (flavonoid) mimosa tannin extracts with concentrated aqueous ammonia has been investigated. For that purpose, catechin was also used as a flavonoid model compound and treated in similar conditions. Solid state CP-MAS 13 C NMR and MALDI-ToF spectroscopy studies revealed that, unlike what was recently theorised, amination is not always regioselective and leading to the conversion of one single OH group in C4鈥 into NH 2 . In the present study, new reactions have been ...
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#1Leila Hojabri (U of A: University of Alberta)H-Index: 14
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A new linear saturated terminal diisocyanate was synthesized from oleic acid via Curtius rearrangement, and its chemical structure was identified by FTIR, 1H and 13C NMR, and MS. The feasibility of utilizing this new diisocyanate for the production of polyurethanes (PUs) was demonstrated by reacting it with commercial petroleum-derived polyols and canola oil-derived polyols, respectively. The physical properties of the PUs prepared from fatty acid-derived diisocyanate were compared to those prep...
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Tannins are soluble, astringent secondary phenolic metabolites generally obtained from renewable natural resources, and can be found in many plant parts, such as fruits, stems, leaves, seeds, roots, buds, and tree barks, where they have a protective function against bacterial, fungal, and insect attacks. In general, tannins can be extracted using hot water or organic solvents from the bark, leaves, and stems of plants. Industrially, tannins are applied to produce adhesives, wood coatings, and ot...
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Abstract Soybean protein isolate (SPI) was tested in this study as a crosslinker and formaldehyde substitute for preparing high biomass content sustainable rigid tannin-furanic-SPI (TFS) and lignin-tannin-furanic-SPI (LTFS) versatile foams. Additionally, flame retardancy was improved by lignin used as a natural fire-retardant. Fourier-transform infrared spectroscopy (FT-IR), coupled with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-MS), revealed a coval...
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It is evident that in the future, the synthesis of polymeric materials will be limited to renewable sources, and incorporation of fossil-based raw materials will be restricted to those from recycled materials. Therefore, there has been an increase in academic and industrial research focused on obtaining different types of high-quality polymers using environmentally friendly alternatives. Tannins are a natural source of polyphenols that are widely distributed in nature. Due to their structural ch...
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Abstract The continuous quest for green and sustainable polymeric material has become a topic of interest. In this context, nonisocyanate polyurethanes (NIPU) materials are considered the best being ecofriendly and nontoxic in nature and have attracted great deal of attention as compared to the conventional polyurethane (PU) obtained from petroleum resources and isocyanates. This review article first highlights the importance of NIPU over the conventional PU. The review further discusses the sum...
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New and emerging demand for polyurethane (PU) continues to rise over the years. The harmful isocyanate binding agents and their integrated PU products are at the height of environmental concerns, in particular PU (macro and聽micro) pollution and their degradation problems. Non-isocyanate poly(hydroxy urethane)s (NIPUs) are sustainable and green alternatives to conventional PUs. Since the early production of the NIPU in 1957, the hybridized NIPU materials have reached their exponential market valu...
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Abstract Recently, tannin furanic resin-based foams exhibiting excellent properties have been developed. However, its friability and thermal insulation must be improved prior to industrialization. Therefore, the tannin preconcentrate from wood bark obtained via liquefaction was mixed with furfuryl alcohol in the presence of a catalyst, surfactant, and solvent. This process includes instant in situ formation of a resin matrix, followed by spontaneous molding and curing to yield a distinct cellula...
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Abstract The extracted tannin from Sumac leaves (Rhus coriaria L.) as a bioresource was utilized for Non-isocyanate Polyurethanes (NIPUs) synthesis. The extracted tannin pre-reacted with dimethyl carbonate. Subsequently, NIPUs were synthesized via the reaction of carbonated tannin with hexamethylene diamine. The condition of the reaction was optimized for different parameters including tannin/DMC weight ratio, reaction time, and reaction temperature by response surface methodology (RSM). The res...
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