Antibacterial and antioxidant bio-based networks derived from eugenol using photo-activated thiol-ene reaction

Modjinou, Tina; Versace, Davy‐Louis; Abbad-Andallousi, Samir; Bousserrhıne, Noureddine; Dubot, Pierre; Langlois, Valérie; Renard, Estelle

doi:10.1016/j.reactfunctpolym.2016.02.002

Cited by 54 publications

(47 citation statements)

References 45 publications

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“…However, the viscosity of pure VE resins is too high for them to be used for common processing technologies. Therefore, VE resins typically need 35–50 wt% of styrene as a low‐viscosity co‐monomer to decrease the viscosity of the resin formulation and copolymerize with VE resin . However, new emission standards for composite manufacturing by the Environmental Protection Agency specifically target styrene as a volatile organic compound (VOC), hazardous air pollutant (HAP) and a potential human carcinogen.…”

Section: Introductionmentioning

confidence: 99%

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Zhang

Thakur

et al. 2018

Polymer International

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A renewable chemical, eugenol, is methacrylated to produce methacrylated eugenol (ME) employing the Steglich esterification reaction without any solvent. The resulting ME is used as a low‐viscosity co‐monomer to replace styrene in a commercial epoxy‐based vinyl ester resin (VE). The volatility and viscosity of ME and styrene are compared. The effect of ME loading and temperature on the viscosity of the VE–ME resin is investigated. Moreover, the thermomechanical properties, curing extent and thermal stability of the fully cured VE–ME thermosets are systematically examined. The results indicate that ME is a monomer with low volatility and low viscosity, and therefore the incorporation of ME monomer in VE resins allows significant reduction of viscosity. Moreover, the viscosity of the VE–ME resin can be tailored by adjusting the ME loadings and processing temperature to meet commercial liquid molding technology requirements. The glass transition temperatures of VE–ME thermosets range from 139 to 199 °C. In addition, more than 95% of the monomer is incorporated and fixed in the crosslinked network structure of VE–ME thermosets. Overall, the developed ME monomer exhibits promising potential for replacing styrene as an effective low‐viscosity co‐monomer. The VE–ME resins show great advantages for use in polymer matrices for high‐performance fiber‐reinforced composites. This work is of great significance to the vinyl ester industry by providing detailed experimental support. © 2018 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Zhang

Thakur

et al. 2018

Polymer International

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“…14 A presença de diferentes grupos na estrutura do eugenol possibilita a preparação de uma gama de substâncias, a citar: poliacetilenos, 15 copoliésteres aromáticos 16 e copolímeros multibloco, 17 os quais se aplicam na indústria de polímeros (Figura 2). Além disso, o uso do eugenol apresenta benefícios para o setor industrial e a sociedade, uma vez que pertencer ao grupo de compostos monoaromáticos livres, enquadrando-se no âmbito de recursos renováveis, 18 O interesse da comunidade científica pelo eugenol é justificado pelo fato do mesmo ser utilizado como material de partida na síntese de diversos produtos naturais e bioativos, 8 como, por exemplo, na síntese do: 6-Gingerol 21 , Cimiracemate B 22 , Imperanene 23 , Obovatol 24 e XH-14 25 (Figura 4).…”

Section: Figura 1 Estrutura Do Eugenolunclassified

“…Na indústria alimentícia e cosmética, o eugenol é utilizado como flavorizante, além de atuar como antioxidante na captura de radicais livres. 26 Na odontologia, o eugenol é utilizado na preparação de resinas dentárias, 18,27 sendo sua primeira utilização datada de 1873 em cavidades dentárias cariadas. 28 O eugenol também exibe uma grande variedade de propriedades biológicas e farmacológicas atuando como: analgésico, antipirético, anestésico, anti-inflamatório, antifúngico, antibacteriano, anticancerígeno, e atividade repelente frente a insetos.…”

Section: Figura 4 Exemplos De Produtos Naturais E Compostos Bioativounclassified

The State of the Art of Eugenol: A Technological Survey Based on Patent and Periodical Database

et al. 2019

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Eugenol is a natural product found in greater quantity in the Eugenia Caryophyllata and exhibits a wide variety of biological and pharmacological applications, making it a product of great commercial interest. Motivated by its applications, this work aimed to investigate the technological potential and the scientific interest of this compound through an analysis of patents databases and indexed journals. The searches were carried out in three patent banks, on the Web of Science platform, and the statistical study was based on the ARIMA (1.1.0) model. The majority of the patent records related to the researched technology had been filed in the Espacenet database and dealt mainly with agriculture and dentistry. A constant linear growth in the number of records of patents granted could be observed over the years, with a remarkable dominance of patents recorded by China (107) followed by the United States (47) and Brazil (22). The h-index for the term eugenol was 107.2 and there was a growing trend of increased patent deposits for the next 50 years. In short, there is great scientific and technological interest, and a strong trend towards increased patent deposits for the next few years on eugenol.

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“…Thiol–ene chemistry was used to prepare antibacterial and antioxidant bio‐based networks that were derived from linalool and eugenol . In this work, a photoinitiated thiol–ene reaction of linalool, a terpene constituent of lavender essential oil, was used in combination with allyl derivative eugenol and trimethylolpropane tris(3‐mercaptopropionate) under solvent‐free conditions to give renewable materials with high cross‐linking densities.…”

Section: Thiol–ene Reaction For the Synthesis Of Terpene‐based Monomementioning

confidence: 99%

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Firdaus

2017

Asian J Org Chem

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This Focus Review highlights the application of thiol-ene (click) chemistry to the productiono fadiverse range of materials that are derived from terpenes. To present an overview concerning the potencyo ft erpenes as renewable resources, recent advances in their developmentb y using synthetic organic chemistry are initially discussed. In addition, the use of thiol-enec hemistry as an efficient approach and versatile tool for noncatalytic carbonÀheteroatom bond formation is briefly presented, including mecha-nistic and kinetic aspects, as well as some structuralc onsiderations,t hat is, the influenceo ft he thiol and olefin structures, which should be well-thought-out before applying such chemistry.T his discussiona lso coversh ow an initiator works and its effect on the reactionr ate. Moreover,t he utilization of thiol-ene reactions for the synthesis of terpenebased valuable platform chemicals, monomers, and polymers, includingr ecent examples that demonstrate its broad utility,a re highlighted.[a] Dr.M.F irdaus Scheme11. Terpene-basedp olythioethers thatwere prepared by thiol-ene photopolymerization. [100] Scheme12. Preparation of cross-linkedthin films that were derived from limonene and their possible addition type. [101] Asian

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Antibacterial and antioxidant bio-based networks derived from eugenol using photo-activated thiol-ene reaction

Cited by 54 publications

References 45 publications

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

The State of the Art of Eugenol: A Technological Survey Based on Patent and Periodical Database

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

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