Naturally occurring phenolic sources: monomers and polymers

Lochab, Bimlesh; Varma, I. K.

doi:10.1039/c4ra00181h

Cited by 250 publications

(170 citation statements)

References 571 publications

(575 reference statements)

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“…As far as eugenol (4-allyl-2-methoxyphenol) is concerned, it is an interesting naturally occurring, renewable phenol compound extracted from plant and some specific lignin [19]. For example, eugenol comprises approximately 70-90% of clove oil from eugenia caryophyllata and occurs widely as a component of essential oils [20] with relatively low cost (ca.…”

Section: Introductionmentioning

confidence: 99%

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

Wan

Gan

et al. 2016

Chemical Engineering Journal

237

138

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Abstract:To develop functional sustainable epoxy resins, we report a novel epoxy resin (DEU-EP) with high net biobased content (70.2 wt%) derived from renewable eugenol. We comparatively study DEU-EP with a commercial bisphenol A epoxy resin (DGEBA) in the presence of a most representative aromatic diamine curing agent, 4,4'-diaminodiphenyl methane (DDM).Differential scanning calorimetry reveals that DEU-EP can be sufficiently cured by DDM at a slower rate than DGEBA. By applying an autocatalytic reaction model, we adequately simulate the curing rate of DEU-EP/DDM, and reveal its detailed kinetic mechanisms from model-free isoconversional analysis. Dynamic mechanical analysis shows that DEU-EP/DDM takes higher storage modulus up to ~97 o C than DGEBA/DDM with the glass temperature of 114 o C. Nanoindentation and thermogravimetric analysis demonstrate that compared with DGEBA/DDM, DEU-EP/DDM exhibits a 20%, 6.7% and 111% increase in Young's modulus, hardness and char yield, respectively. Microscale combustion calorimetry data show that DEU-EP/DDM expresses 55% and 38% lower heat release rate and total heat release than DGEBA/DDM, respectively.Macroscopically, the horizontal burning test approves DEU-EP/DDM can self-extinguish in a short time. Our results demonstrate that the eugenol building blocks and their arrangement greatly affect the cure behaviors of DEU-EP/DDM, and contribute significantly to its enhanced mechanical properties, high-temperature charring ability and chain motions at glass state, as well as the reduced flammability. To summarize, DEU-EP exhibits a high promise as a new sustainable epoxy monomer for fabricating high biobased content, high rigid and low flammable epoxy materials.

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Section: Introductionmentioning

confidence: 99%

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

Wan

Gan

et al. 2016

Chemical Engineering Journal

237

138

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“…[27,33,34] The synthesis of HPPDP involved four steps. The first step is the methyl ether protection of phenolic -OH by reaction with methyl iodide in the presence of potassium hydroxide and DMSO as a solvent.…”

Section: Synthesis Of 4-(4-hydroxyphenoxy)-3-pentadecylphenolmentioning

confidence: 99%

Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

et al. 2014

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A new bisphenol viz., 4-(4-hydroxyphenoxy)-3-pentadecylphenol (HPPDP) was synthesized starting from cashew nut shell liquid (CNSL). Aromatic (co)polyesters containing ether linkages in the main chain and pendent pentadecyl chains were synthesized by the interfacial polycondensation of HPPDP with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol %) and by polycondenation of varying composition of HPPDP and bisphenol-A (BPA) with TPC. The resultant (co)polyesters exhibited inherent viscosities in the range 0.70-1.21 dL g −1 and number-average molecular weights in the range 16,000-48,200 (GPC, polystyrene standard). Polyesters were soluble in common organic solvents such as chloroform and dichloromethane and could be cast into films from chloroform solution. Polyesters exhibited T 10 values in the range 430-455°C and Tg values were in the range 29-202°C. Dynamic mechanical storage modulus and maximum on transition of tan δ curve decreased with increased content of HPPDP in copolyesters. Importantly, the large difference between Tg and T 10 values offers the possibility to process these polyesters in the melt.

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“…driven to the interface, leading to the formation of cross-linked spherical shell. We adopt a "sustainable" approach for the synthesis of cardanol-based benzoxazine (Bz-C), 14,15 where the role of cardanol is extended as a reactive diluent. 16 Conventionally, liquid paraffin is used as a dispersing phase; however, the viscosity of liquid paraffin is not high enough to maintain system stability, 17 so rapid polymerization is needed to prevent the coagulation of the polymerization droplets.…”

Section: Introductionmentioning

confidence: 99%

Interfacial encapsulation of bio‐based benzoxazines in epoxy shells for temperature triggered healing

Sharma

Lochab

Kumar

et al. 2015

J of Applied Polymer Sci

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Successful application of interfacial engineering for the preparation of cross-linked epoxy microspheres containing thermally polymerizable cardanol-based benzoxazine (Bz-C) monomer in the core is demonstrated. Bz-C is facilely synthesized by Mannich type condensation of cardanol (a by-product of cashew nut industry) and aniline with formaldehyde under solventless conditions. The encapsulation process relies on the preferential reaction of polydimethylsiloxane immiscible epoxy resin and amine-based hardener to form a cross-linked spherical shell at the interface. The microcapsule dimensions and core content could be tailored by modulating the operating parameters, particularly stirring speed and Bz-C: epoxy ratio. Spherical microcapsules with a core content of 37% were obtained when the reaction was carried out at 600 rpm, while maintaining the reaction medium at 708C with Bz-C: epoxy ratio of 2.3 : 1. The simplicity and versatility of the present methodology are the forte of this technique, which widens the scope for large-scale application of benzoxazines in the field of temperature triggered healing. V C 2015 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2015, 132, 42832.

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Naturally occurring phenolic sources: monomers and polymers

Cited by 250 publications

References 571 publications

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

Interfacial encapsulation of bio‐based benzoxazines in epoxy shells for temperature triggered healing

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