Cardanol benzoxazines – interplay of oxazine functionality (mono to tetra) and properties

Shukla, Swapnil; Mahata, Arup; Pathak, Biswarup

doi:10.1039/c5ra14214h

Cited by 84 publications

(106 citation statements)

References 48 publications

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“…Likewise, in petro‐sourced monomers, an increase in oxazine functionality reduced the curing temperature. A systematic study of symmetrically designed cardanol monomers with variation in oxazine functionality from 1–4 revealed a significant reduction in curing temperature . The heat of the curing reaction was found to increase with increase in functionalities which aids the ROP reaction confirming their role in cross‐linking reactions.…”

Section: Introductionmentioning

confidence: 92%

“…With an increase in the number of benzoxazine functionality/monomer from 1 to 3, that is, C‐a, C‐ddm, and C‐trisapm, respectively, an improvement in the viscosity, thermal stability, and LSS value (26–100 kg cm −2 ) with a substantial lowering in cure temperature is observed. The improvement in LSS value is accounted for by a higher extension of H‐bonding and cross‐link density network formation within the polymer matrix …”

Section: Applications Of Cardanol Benzoxazinesmentioning

confidence: 99%

“…The adhesive behavior is also utilized for composite applications. A composite based on poly(C‐am) with surface treated jute fibers with alkali of 5–10% strength led to an improvement in resistance at break from 28% and 48%, respectively, which accounted for by the exposition of internal fibrillary structure of jute to promote interfacial adhesion between jute fibers and the benzoxazine matrix …”

Section: Applications Of Cardanol Benzoxazinesmentioning

confidence: 99%

“…The presence of phenolicOH, long alkylene chain, and free ortho ‐ and para ‐ positions in cardanol provides reaction sites for chemical modification to form green synthons suitable in various applications . In general, cardanol and its derivatives are attractive and explored as curing agents, coatings, surfactants, antioxidants, plasticizers, adhesives, and more recently in energy storage applications …”

Section: Introductionmentioning

confidence: 99%

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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.

show abstract

Section: Introductionmentioning

confidence: 92%

Section: Applications Of Cardanol Benzoxazinesmentioning

confidence: 99%

Section: Applications Of Cardanol Benzoxazinesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Cardanol Benzoxazines: A Versatile Monomer with Advancing Applications

Monisha

Amarnath

Mukherjee

et al. 2018

Macro Chemistry & Physics

Self Cite

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“…In that list of renewable alternatives, natural phenols, ie, phenols or phenol derivatives derived from natural resources emerge as a vital class of bio‐derived materials, used for the preparation of commercially potential and industrially valuable polymeric resins such as epoxides and benzoxazines, etc. Among the industrially valuable thermosetting polymeric materials, polybenzoxazines have been shown to improved properties useful for different industrial and engineering applications . In that context, Mannich condensation from amines, phenolic compounds, and formaldehyde is normally used for the synthesis of benzoxazine monomers with no by‐products, and the subsequent cationic ring‐opening polymerization results into final Polybenzoxazines.…”

Section: Introductionmentioning

confidence: 99%

Development and characterization of fully bio‐based polybenzoxazine‐silica hybrid composites for low‐k and flame‐retardant applications

Krishnadevi

Devaraju

Eeda

et al. 2019

Polymers for Advanced Techs

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In the present work, new classes of bio‐based polybenzoxazines were synthesized using eugenol as phenol source and furfurylamine and stearylamine as amine sources separately through solventless green synthetic process routes and were further reinforced with varying percentages (1, 3, 5, and 10 wt%) of silica (from rice husk) to attain hybrid composites. The molecular structure, cure behaviour, thermal stability, dielectric properties, and flame‐retardant behaviour of both benzoxazine monomers and benzoxazine composites were characterized using appropriate modern analytical techniques. The eugenol‐based benzoxazines synthesized using furfurylamine (FBz) and stearylamine (SBz) were cured at 223°C and 233°C, respectively. The differential scanning calorimetry (DSC) data reveal the glass transition temperatures (Tg) of FBz and SBz were 157°C and 132°C, respectively, and the maximum decomposition temperature (Tmax) as obtained from thermogravimetric analysis (TGA), were found to be 464°C and 398°C for FBz and SBz, respectively. The dielectric constants for FBz and SBz obtained at 1 MHz were 3.28 and 3.62, respectively. Furthermore, varying weight percentages (1, 3, 5, and 10 wt%) of 3‐mercaptopropyltrimethoxysilane (3‐MPTMS) functionalized bio‐silica reinforced the composite materials as evidenced by their improved thermal stability and lower dielectric constant. Data obtained from thermal and dielectric studies suggested that these polybenzoxazines could be used in the form of adhesives, sealants, and composites for high performance inter‐layer low‐k dielectric applications in microelectronics.

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Bioinspired Design Provides High‐Strength Benzoxazine Structural Adhesives

Higginson

Malollari

et al. 2019

Angewandte Chemie

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A synthetic strategy to incorporate catechol functional groups into benzoxazine thermoset monomers was developed, leading to a family of bioinspired small‐molecule resins and main‐chain polybenzoxazines derived from biologically available phenols. Lap‐shear adhesive testing revealed a polybenzoxazine derivative with greater than 5 times improved shear strength on aluminum substrates compared to a widely studied commercial benzoxazine resin. Derivative synthesis identified the catechol moiety as an important design feature in the adhesive performance and curing behavior of this bioinspired thermoset. Favorable mechanical properties comparable to commercial resin were maintained, and glass transition temperature and char yield under nitrogen were improved. Blending of monomers with bioinspired main‐chain polybenzoxazine derivatives provided formulations with enhanced shear adhesive strengths up to 16 MPa, while alloying with commercial core–shell particle‐toughened epoxy resins led to shear strengths exceeding 20 MPa. These results highlight the utility of bioinspired design and the use of biomolecules in the preparation of high‐performance thermoset resins and adhesives with potential utility in transportation and aerospace industries and applications in advanced composites synthesis.

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Cardanol benzoxazines – interplay of oxazine functionality (mono to tetra) and properties

Abstract: Cardanol, an agrowaste – solventless synthesis and processability of benzoxazine monomers. Tailoring the polymer properties as a function of oxazine functionality in the monomers.

Cited by 84 publications

References 48 publications

Cardanol Benzoxazines: A Versatile Monomer with Advancing Applications

Cardanol Benzoxazines: A Versatile Monomer with Advancing Applications

Development and characterization of fully bio‐based polybenzoxazine‐silica hybrid composites for low‐k and flame‐retardant applications

Bioinspired Design Provides High‐Strength Benzoxazine Structural Adhesives

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