Synthesis of polycardanol from a renewable resource using a fungal peroxidase from Coprinus cinereus

Kim, Yong Hwan; Won, Keehoon; Kwon, Jeong Mi; Jeong, Hyun Seong; Park, Seung Young; An, Eun Suk; Song, Bong Keun

doi:10.1016/j.molcatb.2005.04.005

Cited by 50 publications

(11 citation statements)

References 20 publications

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“…Synthetic, tailored urushiols have also been proposed by lipase-catalyzed acylation of benzylic OH-groups followed by peroxidase-or laccase-initiated polymerization of the phenol/catechols moiety ( Figure 25). Cardanols are natural phenols structurally related to urusiols and likewise can be polymerized using laccases of peroxidases [32,33,[168][169][170].…”

Section: Artificial Urushimentioning

confidence: 99%

Enzyme Initiated Radical Polymerizations

2012

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Section: Artificial Urushimentioning

confidence: 99%

Enzyme Initiated Radical Polymerizations

2012

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“…Hence, it was used in direct polymerization (Kim et al, 2005), as a polyol for the synthesis of new polyurethanes (Suresh et al, 2005), in polyester formulations (Lespinasse et al, 2011), in thermosets (such as Novolac) (Yadav et al, 2009;Huong et al, 1996), in vinyl ester networks (Sultania et al, 2010) and also in epoxy networks modification (Unnikrishnan et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

A chemical platform approach on cardanol oil: from the synthesis of building blocks to polymer synthesis

Jaillet

Darroman

Boutevin

et al. 2016

OCL

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-This review proposes a platform approach for the synthesis of various building blocks from cardanol oil in one or two-steps synthesis. Cardanol is a natural phenol issued from Cashew nutshell liquid (CNSL). CNSL is a non-edible renewable resource, co-produced from cashew industry in large commercial volumes. Cardanol is non-toxic and particularly suitable as an aromatic renewable resource for polymers and materials. Various routes were used for the synthesis of di-and poly-functional building blocks used thereafter in polymer syntheses. Phenolation was used to dimerize/oligomerize cardanol to propose increase functionality of cardanol. Thio-ene was used to synthesize new reactive amines. Epoxidation and (meth)acrylation were also used to insert oxirane or (meth)acrylate groups in order to synthesize polymers and materials.Keywords: Cardanol / epoxide / acrylate / carbonate / amine / vinyl ester Résumé -Une approche plateforme de l'huile de cardanol : de la synthèse d'intermédiaires réactionnels à la synthèse de polymères. Cet article présente une approche plateforme de synthèse d'intermédiaires réactionnels variés pour l'élaboration de polymères à partir de cardanol. Le cardanol est un phénol naturel issu de l'huile de coque de noix de cajou -Cashew nutshell liquid (CNSL), une ressource renouvelable non-alimentaire coproduit de l'industrie de la noix de cajou. Le cardanol est non-toxique est particulièrement adapté pour l'intégration de noyaux aromatiques dans des polymers et des matériaux biosourcés. Différentes voies ont été envisages pour la synthèse d'intermédiaires réaction-nels di-et poly-fonctionnels pour la synthèse de polymères. La phénolation a été utilisée pour dimériser/oligomériser le cardanol pour augmenter sa fonctionnalité. Le couplage thio-ene a été utilize pour élaborer de nouvelles amines réactives. L'époxidation et la (méth)acrylation ont permis la fonctionnalisation groupes oxirane ou (méth)acrylate afin d'élaborer des matériaux.

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“…Cardanol was already extensively studied for material synthesis, particularly by Wadgaonkar and coworkers [16,17], through direct polymerization [18], as a polyol in new polyurethanes [19], in polyester compositions [20], with partial or total substitution of phenol in thermoset resins such as Novolac resins [9,21,22], vinyl esters [23] and also in epoxy resins modification [24]. But few works reported the epoxidation of cardanol for the synthesis of new epoxy resins.…”

Section: Introductionmentioning

confidence: 99%

New biobased epoxy materials from cardanol

Jaillet

Darroman

Ratsimihety

et al. 2013

Euro J Lipid Sci & Tech

152

123

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Commercial epoxidized cardanol, from cashew nut shell liquid (CNSL), is a biobased epoxide reactant with interesting aromatic structure. Epoxidized cardanol was thoroughly analyzed using 1 H and 13 C NMR, size exclusion chromatography, and titration in order to determine the structure. This epoxidized cardanol was reacted with isophorone diamine and Jeffamine D400 diamine in order to synthesize epoxy networks. These epoxy networks, formulated in stoichiometry ratio, were characterized by differential scanning calorimetry, thermogravimetric analysis, dynamic mechanical analysis analyses and were compared to bisphenol A diglycidyl ether (DGEBA) network. Cardanol-based epoxy materials exhibit interesting mechanical and thermal properties for coatings.Practical application: The reactant described in this contribution, i.e. epoxidized cardanol from CNSL, provides biobased aromatic building blocks for further epoxy resin syntheses by reaction with amine hardeners. The obtained epoxy networks are partially biobased and may be applied as binders and coatings.

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Synthesis of polycardanol from a renewable resource using a fungal peroxidase from Coprinus cinereus

Cited by 50 publications

References 20 publications

Enzyme Initiated Radical Polymerizations

Enzyme Initiated Radical Polymerizations

A chemical platform approach on cardanol oil: from the synthesis of building blocks to polymer synthesis

New biobased epoxy materials from cardanol

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