Synthesis and characterization of resorcinol‐cinnamaldehyde resins

Žigon, Majda; Šebenik, Anton; Osredkar, U.; Vizovišek, I.

doi:10.1002/apmc.1987.051480112

Cited by 12 publications

(6 citation statements)

References 6 publications

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“…B is nonreactive when small amounts of basic catalyst are used. The higher consumption of C is explained by two addition reactions …”

Section: Resultsmentioning

confidence: 99%

“…The second type of reaction (Scheme S2) corresponding to the addition on the carbon 3 of C is confirmed by NMR 1 H spectra in the zone of 4–4.5 ppm. The addition is due to the presence of the carbonyl function and the benzene ring of cinnamaldehyde which makes the double bond polarized …”

Section: Resultsmentioning

confidence: 99%

“…Cinnamaldehyde is commonly used as a natural flavoring and fragrance agent . It is an α,β-unsaturated aldehyde, which is very reactive due to the strong polarization of the π electrons of the double bond due to the vicinity of the benzene ring and of the carbonyl group . Although the condensation of resorcinol with cinnamaldehyde has been reported in the literature, , only novolac RC resins in acid medium have been developed.…”

Section: Introductionmentioning

confidence: 99%

“…It is an α,β-unsaturated aldehyde, which is very reactive due to the strong polarization of the π electrons of the double bond due to the vicinity of the benzene ring and of the carbonyl group . Although the condensation of resorcinol with cinnamaldehyde has been reported in the literature, , only novolac RC resins in acid medium have been developed. Moreover, the addition of hexamethylenetetramine (HMTA) as a curing agent was needed, which limits the applications of these materials as HMTA is toxic, and during curing would decompose into amino-alcohols, ammonia, and formaldehyde condensates …”

Section: Introductionmentioning

confidence: 99%

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Toward Sustainable Phenolic Resins from Biobased Aldehydes Using Spark Plasma Sintering

Moualhi,

Rios De Anda,

Vahabi

et al. 2023

ACS Sustainable Chem. Eng.

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Phenolic resins are an attractive family of thermoset materials. However, there are some concerns related to the high toxic nature of formaldehyde and phenol, i.e., the main building blocks for phenolic resins. Herein, a sustainable alternative method is proposed to synthesize fully biobased and nonharmful resoles based on the condensation of resorcinol (R) with 4-four different aldehydes under alkaline conditions. Two aldehyde-based building blocks including 5-methylfurfural (MFu) and cinnamaldehyde (C) obtained from biobased renewable and abundant resources were successfully formulated with resorcinol, providing more sustainable and environmental-friendly alternatives to current commercially available and hazardous phenol-formaldehyde resins. Two molar ratios of basic catalyst (HO–)/(R) were considered to study their effect on the prepolymerization reaction and on the thermo-mechanical properties of the final materials. The thermal decomposition behavior of the cured resoles was investigated by thermogravimetric analysis (TGA), showing high degradation temperatures and high char yields (up to 60%). Furthermore, the resoles also exhibited high chemical resistance with insoluble fractions (IFs) up to 80%. Finally, to study the mechanical properties of the obtained resoles, the fully cross-linked resoles were consolidated using the spark plasma sintering (SPS) technique. The microstructures of the sintered resoles were investigated by scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS). Compression tests were also conducted to evaluate the mechanical resistance of cured resoles with compression moduli and strength values ranging up to 1.25 GPa and 74 MPa, respectively. Pyrolysis–combustion flow calorimetry analysis (PCFC) revealed that MFu has a very low flammability behavior, demonstrated with a peak of heat release (pHRR) of around 16 W/g and the total heat release (THR) of 2.5 kJ/g. Overall, it was demonstrated that MFu as a nontoxic, biobased, and inexpensive aldehyde can be advantageously used in the preparation of more sustainable phenolic resins.

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“…B is nonreactive when small amounts of basic catalyst are used. The higher consumption of C is explained by two addition reactions …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Toward Sustainable Phenolic Resins from Biobased Aldehydes Using Spark Plasma Sintering

Moualhi,

Rios De Anda,

Vahabi

et al. 2023

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

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“…Several phenol–formaldehyde condensation polymers have been synthesized and used in metal ion adsorption studies. Zigon et al3, 4 synthesized resorcinol–formaldehyde–crotonaldehyde resin in different media, and characterized the polymers. Parmer and coworkers5 synthesized resacetophenone–formaldehyde resin in acidic medium and studied its chelation ion‐exchange properties.…”

Section: Introductionmentioning

confidence: 99%

Chelating resins VI: Chelating resins of formaldehyde condensed phenolic Schiff bases derived from 4,4?-diaminodiphenyl ether with hydroxybenzaldehydes?synthesis, characterization, and metal ion adsorption studies

Samal

Das

Dey

et al. 2000

J. Appl. Polym. Sci.

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Phenolic Schiff bases derived from o‐, m‐, and p‐hydroxybenzaldehydes and 4, 4′‐diaminodiphenyl ether were subjected to polycondensation reaction with formaldehyde. The resins were found to form polychelates readily with several metal ions. The materials were characterized by elemental analysis, GPC, IR, UV‐Vis, 1H‐NMR, XRD, and thermal analyses like TG, DTG, and DSC studies. The 1H‐NMR spectra of the resins provided evidence of polycondensation with well‐defined peaks for bridging methylene and terminal methylol functions. The metal‐ligand bonds were registered in the IR spectra of the polychelates. The thermal analysis data provided the kinetic parameters like activation energy, frequency factor, and entropy changes associated with the thermal decomposition. These data indicated the resins to be more stable than the polychelates. The DSC and XRD data indicated that the incorporation of metal ions significantly enhanced the crystallinity of the polymers. The resins could adsorb several metal ions from dilute aqueous solutions. Adsorption characteristics of the resins towards Cu(II) and Ni(II) were studied spectrophotometrically both in competitive and noncompetitive conditions. The effects of pH, contact time, quantity of the sorbent, concentration of the metal ions in a suitable buffer medium were studied. The resins were found to be selective for Cu(II) leading to its separation from a mixture of Cu(II) and Ni(II). © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 77: 967–981, 2000

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Synthesis and characterization of resins from 4‐ethylphenol and cinnamaldehyde

Šebenik

Žigon

Osredkar

1988

Angew. Makromol. Chem.

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The mechanisms of the reaction between 4-ethylphenol and cinnamaldehyde were studied by means of HET 2DJ I3C-NMR spectroscopy, H-NMR spectroscopy and GPC. In the first step of the reaction the addition of Cethylphenol to carbonyl group and to double bond of cinnamaldehyde takes place. In the second step of the reaction the -CH(OH)-group reacts with Cethylphenol to form branched products of red coloured resins with an average molecular weight of 600. The reaction takes place at temperatures above l00OC in strong acid medium. ZUSAMMENFASSUNG:Es wurde der Mechanismus der Reaktion von CEthylphenol mit Zimtaldehyd mittels HET 2DJ I3C-NMR Spektroskopie, ' H-NMR Spektroskopie und GPC untersucht. In der ersten Stufe findet die Addition des CEthylphenols an die Carbonylgruppe und an die Doppelbindung des Zimtaldehyds statt. In der zweiten Stufe reagiert die -CH(OH)-Gruppe mit CEthylphenol und bildet verzweigte Produkte in ratlich gefitrbten Harzen mit einem Durchschnittsmolekulargewicht von 600. Die Reaktion verliiuft bei Temperaturen tiber 100°C in stark saurem Medium.

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Synthesis and characterization of resorcinol‐cinnamaldehyde resins

Cited by 12 publications

References 6 publications

Toward Sustainable Phenolic Resins from Biobased Aldehydes Using Spark Plasma Sintering

Toward Sustainable Phenolic Resins from Biobased Aldehydes Using Spark Plasma Sintering

Chelating resins VI: Chelating resins of formaldehyde condensed phenolic Schiff bases derived from 4,4?-diaminodiphenyl ether with hydroxybenzaldehydes?synthesis, characterization, and metal ion adsorption studies

Synthesis and characterization of resins from 4‐ethylphenol and cinnamaldehyde

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