Reaction of condensed tannins with ammonia

Published on Jan 1, 2013in Industrial Crops and Products5.645
· DOI :10.1016/J.INDCROP.2012.11.024
Flavia Lega Braghiroli15
Estimated H-index: 15
 (University of Lorraine), Vanessa Fierro62
Estimated H-index: 62
 (University of Lorraine)+ 5 AuthorsAlain Celzard68
Estimated H-index: 68
 (University of Lorraine)
Sources
Abstract
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′ into NH 2 . In the present study, new reactions have been evidenced, clearly leading to multiamination of several phenolic hydroxyl groups, heterocycle opening, and oligomerisation and cross-linking through the formation of N bridges between flavonoid units.
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#1Koh HashidaH-Index: 10
#2Rei MakinoH-Index: 8
Last. Seiji OharaH-Index: 15
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Deodorizing effects of tea catechins on amines were examined under alkaline conditions to eliminate the neutralization reaction. They showed deodorizing activity on ethylamine, but none on dimethylamine or trimethylamine. Deodorizing activity on ethylamine was found to be in the order of (−)-epigallocatechin gallate > gallic acid > (−)-epigallocatechin (EGC) > (−)-epicatechin gallate >ethyl gallate>> (+)-catechin=(−)-epicatechin. Further, reaction products of EGC with methylamine, ethylamine, an...
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A thermomechanical analysis (TMA) study, directly on a bonded joint during the process of adhesive hardening, on the sinergy and interference between polycondensation and autocondensation on procyanidin, and profisetinidin–prorobinetinidin-type polyflavonoid tannins network formation and hardening, confirmed that also at the higher curing temperatures characteristic of the hardening of tannin-based wood adhesives, hardening by polycondensation can be coupled with simultaneous hardening of tannin...
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The curves of increase of modulus as a function of temperature obtained by thermomechanical analysis (TMA) of joints bonded with different polyflavonoid tannins–hardener systems show a succession of different plateaus. Equally, the increase of modulus first-derivate curves show a succession of several peaks. Both the position and extent of the plateaus of the modulus curve as well as the peaks of its first derivate curve show considerable apparent variability in relative intensity and sometime i...
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Apr 11, 1997·Journal of Applied Polymer Science3.13
#1E. MassonH-Index: 12
#2Antonio PizziH-Index: 80
Last. M. MerlinH-Index: 2
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Comparative kinetics of the radical autocondensation induced by SiO 2 on a series of polyflavonoid tannins, namely, pine, pecan, mimosa, quebracho, gambier, sumach, and on the catechin monomer as a model compound were carried out by electron spin resonance. The induced radical autocondensation appeared to be independently catalyzed by the known base mechanism, as well as SiO 2 and Lewis acid attack directly at the heterocycle oxygen. The reaction occurs in two definite steps: the first, the radi...
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Jun 6, 1996·Journal of Applied Polymer Science3.13
#1E. MassonH-Index: 12
#2Antonio PizziH-Index: 80
Last. A. MerlinH-Index: 4
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Cellulose surface catalysis of the induced autocondensation of tannins has been found to occur also for the radical mechanism of the reaction. Equally effective in accelerating pyran ring opening of polyflavonoids by radical mechanisms appears to be the presence of any substance leading to micellar structures in the tannin solution. Thus, soaps and synthetic and natural polymeric colloids have been found to accelerate the reaction. The micellar effect is distinct and different from the surface c...
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Apr 11, 1996·Journal of Applied Polymer Science3.13
#1E. MassonH-Index: 12
#2A. MerlinH-Index: 4
Last. Antonio PizziH-Index: 80
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Comparative kinetics of the radical autocondensation induced by SiO2 of a polyflavonoid tannin, namely quebracho tannin a mostly profisetinidin/prorobinetinidin tannin, in its natural extract state, sulfited, carbohydrate free, and in its adhesive intermediate form were carried out by electron spin resonance (ESR). The results obtained not only confirmed the existence of strong radical mechanisms of tannin autocondensation in the presence of dissolved SiO2, but also pointed out new effects of in...
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#1Antonio PizziH-Index: 80
Brief Nonmathematical Review of Adhesion Theories as Applicable to Wood Urea-Formaldehyde Adhesives Melamine-Formaldehyde Adhesives Phenolic Resin Wood Adhesives Tannin-Based Wood Adhesives Lignin-Based Wood Adhesives Resorcinol Adhesives Diisocyanate Wood Adhesives.
Mar 28, 1994·Journal of Applied Polymer Science3.13
#1Antonio Pizzi (University of the Witwatersrand)H-Index: 80
#2A. Stephanou (University of the Witwatersrand)H-Index: 11
Water solutions of 40–50% polyflavonoid tannin extracts appear to be in a colloidal state. This is caused by both the presence of noticeable amounts of hydrocolloid gums as well as the presence of higher molecular mass tannins. 13C NMR analysis appears to confirm that during chemical treatment, reactions occur in these colloidal solutions that would not be likely to occur in noncolloidal solutions as used in model compound experiments. These reactions centre on the role of the organic anhydride ...
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#1Antonio Pizzi (University of the Witwatersrand)H-Index: 80
#2A. Stephanou (University of the Witwatersrand)H-Index: 11
Chemical and heat treatments introduce noticeable modifications on the structure of four different polyflavonoid tannin extracts during their modification for use as tannin-form aldehyde polycondensates. Such modifications are performance determining and account for the profound differences in behaviour of the four tannin extracts when used as tanninformaldehyde adhesives. Such modifications are directly followed by 13C NMR on the tannin extracts. Although some of the modifications observed by 1...
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12
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Abstract null null It is of practical significance to develop a heparin-free hemodialysis membrane that can be used for clinical applications in a simple way. In this work, a heparin-like coating loaded with null SO3− and null COOH was formed on a polyethersulfone (PES) ultrafiltration membrane by the hydrophobic interactions and hydrogen bonding of tannic acid (TA) with the PES membrane, the cross-linking of D-asparagine (DAS) with TA, and a Michael addition reaction of sodium 3-mercapto-1-prop...
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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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Each day, varying amounts of undigested or partially digested proteins reach the colon where they are metabolized by the microbiota, resulting in the formation of compounds such as ammonia, p-cresol, skatole, phenol, indole, and hydrogen sulfide (H2S). In farm animals, the excessive production of these metabolites can affect the quality of meat and milk and is a source of contaminating emissions from animal manure. In humans, their accumulation is potentially harmful, and it has been proposed th...
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In this study, the tannins extracted from the Pinus radiata bark were used to develop an active–passive dual paint scheme with intumescent (IN) and fire-resistant (FR) behaviors. The properties of the coating were observed to depend on the concentration of high-molecular-weight tannins (H-MWT) incorporated into the formulation. At high concentrations (13% w/w), the coating exhibits fire-retardant properties due to the generation of a carbonaceous layer; however, at low concentrations (2.5% w/w),...
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Collagen powder hydrolysates were reacted with a solution of commercial mimosa bark tannin extract. The mix- ture was prepared at ambient temperature and prepared at 80°C to determine what reactions, if any, did occur between the collagen protein through its amino acids and the polyphenolic condensed tannin. The reaction pro- ducts obtained were analyzed by matrix assisted laser desorption ionization time-of-flight (MALDI ToF) mass spectrometry. Reactions between the two materials did appear to ...
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Human health problems and formaldehyde emission from wood-based composites are some of the major drawbacks of the traditional synthetic adhesives such as urea formaldehyde resins. There have been many attempts to decrease formaldehyde emission and replace urea formaldehyde resins with bio-based adhesives for wood-based composites. Because of some weakness in soy-based adhesive, chemicals have been used as modifiers. Modified soy-based adhesives without any formaldehyde have been successfully use...
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Abstract Flocculants and coagulants market is expected to grow in a Compound Annual Growth Rate (CAGR) of 5.9% between 2017 and 2022. The development of non-pollutant coagulants/flocculants aiming to replace conventional ones, usually toxic, has been extensively studied and one alternative is the possibility of obtaining tannin-based flocculants, compounds present in many plants and easily extracted. However, in order to use tannins as flocculants, their cationization is necessary, which is norm...
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Tannins are eco-friendly, bio-sourced, natural, and highly reactive polyphenols. In the past decades, the understanding of their versatile properties has grown substantially alongside a continuously broadening of the tannins’ application scope. In particular, recently, tannins have been increasingly investigated for their interaction with other species in order to obtain tannin-based hybrid systems that feature advanced and/or novel properties. Furthermore, in virtue of the tannins’ chemistry an...
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