Spectral and thermal studies on the synthesis and catalyzed oligomerization of novel cardanol-based benzoxazines

Kotzebue, Lloyd Ryan Viana; Ribeiro, Francisco Wanderson Moreira; Sombra, Venícios Gonçalves; Feitosa, Judith P.A.; Mele, Giuseppe; Mazzetto, Selma Elaine; Lomonaco, Diego

doi:10.1016/j.polymer.2016.04.005

Cited by 34 publications

(19 citation statements)

References 27 publications

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“…The endothermic events observed in thermograms of compounds 2 to 6 are related to the melting points of these monomers, reflecting the high purity of the monomers prepared. Exceptionally, endothermic peak was absent on compound 7 (GU‐thf) that was liquid at room temperature and are in agreement with previous results reported in the literature . The exothermic events represent the polymerization temperature range (from 200 to 290 °C) of the bio‐based benzoxazines.…”

Section: Resultssupporting

confidence: 90%

“…Biomass derived amines were explored in the synthetic route of benzoxazines. Furfurylamine and its hydrogenated derivative, tetrahydrofurfurylamine, are structures obtained from furfural, an organic compound obtained through hydrolysis and dehydration of the xylan presented in most of the agricultural byproducts (corncobs, oat, bran) . As phenols are chemical compounds widely available in nature, they are the most studied starting materials described in the scientific literature for the synthesis of eco‐friendly benzoxazine monomers.…”

Section: Introductionmentioning

confidence: 99%

“…As phenols are chemical compounds widely available in nature, they are the most studied starting materials described in the scientific literature for the synthesis of eco‐friendly benzoxazine monomers. Cardanol, urushiol, vanillin, guaiacol, eugenol, and coumarins are some of the examples of biomass‐based feedstock used in substitution for petroleum‐derived chemicals. Although naturally occurring phenols comprise a wide variety of chemical structures, a few of them are already available in large scales, like cardanol, from cashew industry; or can be potentially produced from renewable feedstock, like vanillin and guaiacol, from lignin.…”

Section: Introductionmentioning

confidence: 99%

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Microwave‐assisted solvent‐free synthesis of novel benzoxazines: A faster and environmentally friendly route to the development of bio‐based thermosetting resins

Oliveira

Kotzebue

Ribeiro

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Microwave-assisted organic synthesis (MAOS) is a well-established technique that has been used in the enhancement of chemical reactions. Here, the versatility of MAOS is explored describing an environmentally friendly one-pot route to novel bio-based benzoxazines under solvent-free conditions. The lignin derivative, guaiacol, along with paraformaldehyde and different conjugated and nonconjugated amines are successfully fused into guaiacol-derived 3,4-dihydro-2H-1,3-benzoxazines. The reactions conducted under microwave irradiation are completed much faster than those under traditional heating, reducing the reaction time from hours to only 6 min, with good yields. The chemical structures of novel benzoxazines are confirmed by 1 H and 13 C NMR spectroscopy, FTIR, and HR-MS. The thermal behavior of the resins are evaluated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), showing that these polymers have good thermal stability and wide processing-window, with onset temperature of polymerization above 230 8C. These results indicate dramatic improvement over the traditional methodologies for the production of this class of resins, which are usually obtained by time-consuming procedures and in the presence of toxic solvents. Therefore, MAOS can be considered a green and efficient strategy for the synthesis of eco-friendly benzoxazines.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Microwave‐assisted solvent‐free synthesis of novel benzoxazines: A faster and environmentally friendly route to the development of bio‐based thermosetting resins

Oliveira

Kotzebue

Ribeiro

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…are studied. Monofunctional cardanol benzoxazine is obtained when reacted with substituted aliphatic and aromatic mono‐amines such as cyclohexylamine (cha), tetrahydrofurfurylamine (thfa) allylamine (aa), 3‐aminopropyltriethoxysilane (ameo), benzylamine (ba) N,N ‐dimethylaminopropylamine (dmapa), 4‐nitroaniline (na), 2‐aminopyridine (py), 2‐amino‐5‐methylpyridine (mpy), 4‐fluoroaniline (fla), 4‐bromoaniline (bra), 4‐cyanoaniline (cna), 4‐chloroaniline (cla), 4‐aminophenol (ap), 4‐aminobenzoic acid (aba), 4,4′‐aminophenoxy itaconimide (dde‐i), or nadimide (dde‐n) . Polymer‐origin amines either of commercial origin such as polyether monoamine (Jeffamine M‐1000, ja) or modified polymeric amines such as caprolactam amine (cm‐dmapa) are also investigated …”

Section: Introductionmentioning

confidence: 99%

Cardanol Benzoxazines: A Versatile Monomer with Advancing Applications

Monisha

Amarnath

Mukherjee

et al. 2018

Macro Chemistry & Physics

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Polybenzoxazines are evolving as a new class of phenolic resins with a tremendous amount of applications. The ease of structural designing, synthetic procedure, and polymerization reactions are attractive to affect their properties ensuing as an effective substitute for many existing polymers. The nonrenewable origin, toxicity, and increasing cost of petro‐based raw materials are alarming issues. Therefore, the emergence of sustainable benzoxazines, especially based on naturally abundant, agro‐waste origin cardanol is encouraging as it allows both solventless synthesis of monomers and processing to form highly thermally stable thermoset resins. The inherent functionalities in cardanol benzoxazine provide a platform for further structural modifications to advance their applications as adhesives, composites, and energy storage devices.

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“…Kotzebue et al synthesized new cardanol-based benzoxazines (named C-a, C-ch, C-cy,C-thf; Fig. 2), described their complete polymerization under mild conditions using magnesium chloride as a catalyst, obtained soluble polybenzoxazines [23]. All the soluble polybenzoxazines can be used as solution-processed polymers, because they are completely soluble in toluene, chloroform, and dichloromethane, widening its application range [23].…”

mentioning

confidence: 99%

Recent Development of Cardanol Based Polymer Materials-A Review

Jia¹,

Song²,

Li³

et al. 2019

Journal of Renewable Materials

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Polymers from renewable resources are receiving tremendous attention due to the increasing concerns on the depletion of fossil oils and deteriorated environments. Cardanol, as an abundant and renewable chemical raw material, has been widely used for the production of renewable polymer materials via converting into various of chemical monomers with active functional groups. This comprehensive review deals with various aspects of cardanol as a starting material the preparing various polymer and polymer composites such as benzoxazine resins, phenolic resin, polyurethanes, epoxy resin, vinyl ester polymers, polyamide and cyanate ester resins. The assessment of the future prospects for the use of cardanol to synthesise novel and valuable renewable materials is presented.

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Spectral and thermal studies on the synthesis and catalyzed oligomerization of novel cardanol-based benzoxazines

Cited by 34 publications

References 27 publications

Microwave‐assisted solvent‐free synthesis of novel benzoxazines: A faster and environmentally friendly route to the development of bio‐based thermosetting resins

Microwave‐assisted solvent‐free synthesis of novel benzoxazines: A faster and environmentally friendly route to the development of bio‐based thermosetting resins

Cardanol Benzoxazines: A Versatile Monomer with Advancing Applications

Recent Development of Cardanol Based Polymer Materials-A Review

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