Synthesis and characterization of novel bio-based benzoxazines from eugenol

Periyasamy, Thirukumaran; Shakila, A.; Sarojadevi, M.

doi:10.1039/c3ra46582a

Cited by 152 publications

(125 citation statements)

References 19 publications

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“…, which confirms the presence of a benzene ring with an oxazine ring attached to it [11,14]. The peaks at 2,924 and 2,854 cm 21 are due to the asymmetric and symmetric stretching vibrations of the methylene group of the oxazine ring as well as alkyl side chain of eugenol [15,16].…”

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confidence: 69%

Synthesis and characterization of new polybenzoxazines from renewable resources for bio‐composite applications

et al. 2014

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Renewable natural resources such as eugenol, furfurylamine, stearylamine, and jute fiber were used to prepare polybenzoxazine composites. The purity of eugenol which is extracted from clove was confirmed by gas chromatography. FTIR, 1H, and 13C NMR spectroscopic analysis were used to determine the structure of eugenol and the benzoxazine monomers namely 6‐allyl‐3‐furfuryl‐8‐methoxy‐3,4‐dihydro‐2H‐1,3‐benzoxazine (EF‐Bz) and 6‐allyl‐3‐octadecyl‐8‐methoxy‐3,4 dihydro‐2H‐1,3‐benzoxazine (ES‐Bz) synthesized from it. The curing analysis from differential scanning calorimetric analysis shows that the onset of curing is shifted to lower temperature (161°C) for EF‐Bz, when compared with ES‐Bz (174°C). The thermal stability analyzed from thermogravimetric analysis shows that the polybenzoxazine EF‐Pbz has higher thermal stability (T5% = 361°C) with that of ES‐Pbz (T5% = 313°C). The storage modulus, tensile, and flexural strength of the EF‐Bz/Jute fiber composite show high value when compared with ES‐Bz/Jute fiber composites. POLYM. COMPOS., 37:1821–1829, 2016. © 2014 Society of Plastics Engineers

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confidence: 69%

Synthesis and characterization of new polybenzoxazines from renewable resources for bio‐composite applications

et al. 2014

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“…3 shows the evolution of the curing exotherm depending on the P:E ratio. 16 Even if the diamine used is quite different in our case, the properties of the polymerized samples are clearly driven by the rate of benzoxazine ring attached to the phenol while the benzoxazine ring attached to the eugenol seems to be inactive. It appears from these observations that a larger window of processability for the eugenol-rich benzoxazines is achieved.…”

Section: Curing Proceduresmentioning

confidence: 66%

“…Nevertheless, the main interesting characteristic of benzoxazines is their straight and easy synthesis by a Mannich-40 like condensation of three compounds: a phenol, an amine and formaldehyde. [16][17][18][19] Additionaly, except an article, 17 the first studies of eugenol-based benzoxazine did not mention the drastic thermal degradation of the eugenol-based monomers 60 during the curing procedure. 7 The number of newly synthesized monomers is therefore constantly 45 increasing.…”

Section: Introductionmentioning

confidence: 99%

Eugenol-based benzoxazine: from straight synthesis to taming of the network properties

et al. 2015

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Mixed benzoxazine precursors were synthesized using a blend of eugenol, a natural renewable product, and phenol. The structures of 15 these mixed benzoxazine precursors with different phenol:eugenol compositions were attested by 1 H NMR. Their polymerization and degradation were investigated and monitored by DSC and TGA and showed an enhancement of the crosslinking ability with the phenol content. Depending on its relative content, the phenol moiety proved to limit the thermal degradation of the bis-benzoxazine "hybrid" monomer and allowed the formation of crosslinked networks with high thermomechanical stabilities. The properties of the networks were closely dependent on the phenol : eugenol ratio, which allowed for an adjustment of the crosslinking density and a fine tuning of the 20 glass transition temperature (T g ) within a wide temperature range. A comparison between the polymerized hybrid precursors and blend of two pure monomers displaying the same overall composition showed the same material properties increasing the tune-ability of the system. The eugenol/phenol combination for the preparation of mixed/hybrid benzoxazines or corresponding blends clearly paves the way to new sustainable high performance bio-based materials. 25

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“…[4][5][6][7][8] These fascinating characteristics make polybenzoxazine resins a promising candidate in different application areas, for example, electronics, space-ight and aerospace. [10][11][12][13][14][15] Cardanol is an industrial yellow oil extracted from cashew shell liquid (CNSL), which is also a promising renewable phenol resource. [10][11][12][13][14][15] Cardanol is an industrial yellow oil extracted from cashew shell liquid (CNSL), which is also a promising renewable phenol resource.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel biobased benzoxazines from cardbisphenol and the properties of their polymers

Yan

2015

RSC Adv.

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Two types of novel biobased benzoxazine monomers (named as CBB and CBF, respectively) from cardbisphenol were synthesized by a solventless method. The chemical structure of the monomers was confirmed by FTIR, 1 H NMR and 13 C NMR spectra, etc. FTIR and DSC showed that CBB and CBF were thermally initiated and polymerized via ring-opening polymerization. As a result, the thin polybenzoxazine (named as PCBB and PCBF, respectively) films can be obtained. Dynamic mechanical analysis (DMA) indicated that the glass transition temperatures (T g ) of PCBB and PCBF were 94 C and 121 C, respectively. Thermogravimetric analysis (TGA) demonstrated that the thermal stability of PCBF was better that of PCBB. Both PCBB and PCBF had low humidity absorption values.

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Synthesis and characterization of novel bio-based benzoxazines from eugenol

Cited by 152 publications

References 19 publications

Synthesis and characterization of new polybenzoxazines from renewable resources for bio‐composite applications

Synthesis and characterization of new polybenzoxazines from renewable resources for bio‐composite applications

Eugenol-based benzoxazine: from straight synthesis to taming of the network properties

Synthesis and characterization of novel biobased benzoxazines from cardbisphenol and the properties of their polymers

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