Synthesis and Characterization of Tetra-Functional Epoxy Resins from Rosin (original) (raw)
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Rosin based epoxy coating: Synthesis, identification and characterization
European Polymer Journal, 2015
Ketone type derivative of rosin was prepared by dehydrocarboxylation of isomerized abietic acid. Coupling of dipimaryl ketone with maleic anhydride was performed by acetic acid catalyzed Diels-Alder reaction. Afterwards, the dipimaryl ketone was epoxidized to get the corresponding tetra glycidyl ester. The chemical structure of the synthesized products was confirmed by UV, FTIR and 1 H NMR spectroscopic analyses. Cured resins using a rosin-based crosslinker and p-phenylene diamine (a commercial crosslinker) were evaluated using dynamic mechanical analysis (DMA), thermogravimetric analysis (TGA) and some preliminary universal coating tests. Results showed that the fully rosin-based epoxy system gave better performance than commercially bisphenol-A based one. This finding was attributed to a liquid crystal behavior of the rosin-based crosslinker. Mesomorphic transition temperature and liquid crystalline texture of the rosin-based crosslinker were investigated by polarized optical microscopy (POM) and differential scanning calorimetry (DSC).
Study on Synthesis and Performance of Rosin-Derived Polyamide as Epoxy Curing Agent
Abstract-Rosin is an abundantly available natural product. The rosin-based polyamide (RBPA) was synthesized and studied as epoxy curing agent in the paper. The performance of thecured products of epoxy resin/RBPA composites was characterized by FT-IR, TGA and tensile machine. It was found that epoxy resin/RBPA system can cured completely at mass ratio of 100:51 under the condition of room temperture for 6 h, and then 80 ºC for 4 h, the shear strength of epoxy resin/RBPA system was 21.6 MPa, the thermal decomposition temperatures of the cured products of the cured system was 343.0 ºC , glass transition temperatures was 146.6 ºC . Rosin-based polyamide has a great potential to replace some of current petroleum-based compounds in the synthesis of epoxy curing agents.
Express Polymer Letters, 2020
Multifunctional bio-based epoxy resin (PEMPAE) was synthesized by reacting Diels-Alder adduct of gum rosin and maleic anhydride (MPA) with pentaerythritol to get the esterified product (PEMPA) which was further epoxidized using epichlorohydrin and potassium hydroxide. This paper includes the synthesis of bio-based imidoamine curing agent (IAEDK) by reacting diamino diphenyl ether (DDE) with dimaleopimaryl ketone (DMPK), a dehydrodecarboxylated derivative of MPA. The synthesized products were characterized by Fourier transform infrared Spectroscopy (FTIR), proton and 13 C nuclear magnetic resonance spectroscopy (1 H-NMR and 13 C-NMR). Curing dynamics of rosin-based epoxy cured with rosinbased imidoamine crosslinker were evaluated using differential scanning calorimetry (DSC) and were compared with resin cured with synthesized DMPK and commercial DDE curing agents. The mechanical properties and thermal stability of the cured epoxy samples were evaluated using a universal testing machine (UTM) and thermogravimetric analyzer (TGA), respectively. The chemical resistance of the samples was determined in terms of % weight loss when immersed in NaOH, HCl and NaCl solutions. The morphological changes were also evaluated via scanning electron microscopy (SEM). Results revealed that rosin-based epoxy cured with imidoamine curing agent gave preeminent properties over the commercial one. The studies suggested that curing properties were greatly affected by the molecular topology and kind of curing agent used.
Epoxidized rosin acids as co-precursors for epoxy resins
2014
A series of novel epoxy resins were prepared from chemically modified rosin, mainly constituted of abietic acid, diglycidyl ether of bisphenol-A (DGEBA) in different percentages as co-reactants, and isophorone diamine as cross-linking agent. Reactive epoxide groups were introduced in the structure of this common pine tree derivative. The chemical structures of various epoxidized rosin acids precursors were confirmed by NMR spectroscopy. Differential scanning calorimetry and dynamic mechanical analysis were used to determine the glass transition temperature and the elastic modulus of the cured epoxy resins. Relatively rigid materials with thermo-mechanical properties depending on the structure of rosin acid derivatives and their ratios with DGEBA were obtained. Epoxy precursors based on renewable rosin can be efficiently used as co-additives of DGEBA for epoxy products.
Rosin-derived imide-diacids as epoxy curing agents for enhanced performance
Bioresource Technology, 2010
Two rosin-based imide-diacids were synthesized and studied as epoxy curing agents. In comparison, a similar imide-diacid based on trimellitic anhydride was also prepared. The chemical structures were confirmed by 1 H NMR and FT-IR. The curing of a commercial epoxy with these imide-containing diacids was studied by differential scanning calorimetry (DSC). Thermal stability, tensile and dynamic mechanical properties of the cured epoxies were investigated. The results indicate that rosin-based imide-diacids used as curing agents resulted in significantly higher glass transition temperature, tensile and dynamic mechanical properties than the imide-diacid derived from trimellitic anhydride. Rosin acids have a great potential to replace some of current petroleum-based compounds in the synthesis of epoxy curing agents.
Polymer International, 2014
In this study, an epoxy based on eugenol and an anhydride curing agent based on rosin were prepared. Curing of the eugenol epoxy with a commercial anhydride curing agent and with the rosin-derived anhydride curing agent was studied. For comparison, a commercial bisphenol A type epoxy, DER353, was also selected in the curing study. The syntheses of the eugenol epoxy and rosin anhydride were investigated and the chemical structures of the products and intermediates were characterized using 1 H NMR and Fourier transform infrared spectroscopies. Non-isothermal curing of the eugenol epoxy with hexahydrophthalic anhydride and the rosin-derived maleopimaric acid was studied using differential scanning calorimetry. Thermomechanical properties and thermal stability of the cured epoxy resins were evaluated using dynamic mechanical analysis and thermogravimetric analysis, respectively. Addition of 2-ethyl-4-methylimidazole as catalyst greatly decreased the curing temperature and promoted the completion of cure reactions. The results suggest that the eugenol epoxy and the bisphenol A type epoxy have similar reactivity, dynamic mechanical properties and thermal stability.
Curing of epoxy resin using imide-amines
Journal of Applied Polymer Science, 2006
The curing behavior of diglycidyl ether of bisphenol-A (DGEBA) was investigated by differential scanning calorimetry, using varying molar ratios of imide-amines and 4,4′-diaminodiphenyl sulfone (DDS). The imide-amines were prepared by reacting 1 mol of pyromellitic dianhydride (P) with excess (2.5 mol) of 4,4′-diaminodiphenyl ether (E), 4,4′-diaminodiphenyl methane (M), or 4,4′-diaminodiphenyl sulfone (S) and designated as PE, PM, PS. Structural characterization was done using FTIR, 1H NMR, 13C NMR spectroscopic techniques and elemental analysis. The mixture of imide-amines and DDS at ratio of 0 : 1, 0.25 : 0.75, 0.5 : 0.5, 0.75 : 0.25, and 1 : 0 were used to investigate the curing behavior of DGEBA. The multiple heating rate method (5, 10, 15, and 20°C/min) was used to study the curing kinetics of epoxy resins. The peak exotherm temperature was found to be dependent on the heating rate, structure of imide-amine, and also on the ratio of imide-amine : DDS used. Activation energy was highest in case of epoxy cured using a mixture of DDS : imide-amine of a ratio of 0.75 : 0.25. Thermal stability of the isothermally cured resins was also evaluated in a nitrogen atmosphere using dynamic thermogravimetry. The char yield was highest in case of resins cured using mixture of DDS : PS (0.25 : 0.75; EPS-3), DDS : PM (0.25 : 0.75; EPM-3), and DDS : PE (0.75 : 0.25; EPE-1). © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 3502–3510, 2006
Journal of Applied Polymer Science, 2009
Five blend samples of cardanol-based epoxidized novolac resin containing varying concentrations of carboxyl-terminated poly(butadiene-co-acrylonitrile) (CTBN) ranging between 0 and 25 wt % with an interval of 5 wt % were prepared. The epoxidized novolac resin (ECF) was synthesized from the epoxidation of cardanol-based novolac-type phenolic resin (CF) with molar excess of epichlorohydrin (i.e., about 10 mol at 120°C in basic medium). The CF resin was synthesized with a molar ratio of 1 : 0.5 of CF using dicarboxylic acid catalyst such as succinic acid at 120°C for 5 h. The pure epoxy and its blend were cured with stoichiometric amounts of polyamine curing agent. The formation of various products during the synthesis of cardanol-based novolac resin, epoxidized novolac resin, and blending of epoxidized novolac resin with CTBN have been studied by Fourier transform infrared (FTIR) spectroscopic analysis. Further, a reaction mechanism for the step-growth reaction was proposed on the basis of the results of FTIR analysis. Also, the structures of CF and ECF were proposed on the basis of the results of nuclear magnetic resonance and MALDI-TOF mass spectroscopic analysis along with gel permeation chromatographic (GPC) analysis. GPC analysis resulted in Mn of 670 gmol−1. The blend sample having 15 wt % CTBN concentration showed minimum cure time, whereas the presence of CTBN in blend systems showed marginal change in the values of ΔH. A clear-cut two-step mass loss in dynamic thermogravimetric trace of unmodified and CTBN-modified systems was observed. Thermal stability of the blend sample containing 15 wt % CTBN into the pure epoxy resin was the highest among all other prepared systems. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009
Synthesis and characterization of oligosalicylaldehyde-based epoxy resins
Chemical Papers, 2006
The synthesis of a new epoxy resin of oligosalicylaldehyde by the reaction with epichlorohydrin is reported. New resin's epoxy value and chlorine content were determined and found to be 25 % and 1 %, respectively. The characterization of the new resin was instrumented by FTIR, 1 H NMR, scanning electron microscopy, and thermal gravimetric analyses. TGA results showed that the cured epoxy resin has a good resistance to thermal decomposition. The mass losses of cured epoxy resin were found to be 5 %, 10 %, 50 % at 175 • C, 240 • C, and 400 • C, respectively. On the curing procedure the resin was cured with polyethylenepolyamine at 25 • C for 8 h and 100 • C for 1.5 h. The FTIR spectrum of new epoxy resin gave the peak of oxirane ring atν = 918 cm −1 .