Synthesis, characterization, antibacterial and corrosion protective properties of epoxies, epoxy-polyols and epoxy-polyurethane coatings from linseed and Pongamia glabra seed oils

Sharmin, Eram; Ashraf, S. M.; Ahmad, Sharif

doi:10.1016/j.ijbiomac.2006.10.002

Cited by 110 publications

(77 citation statements)

References 28 publications

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“…Increasing the desaturation of C18 fatty acids seemed to greatly facilitate their epoxidation (Table 1). We have confirmed this result by incubating [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C]linoleic and [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C]linolenic acids in the presence of cumene hydroperoxide and PXG4. Epoxidation occurred readily, i.e.…”

Section: Pxg4 Is a Regioselective Peroxygenasementioning

confidence: 56%

“…8B). In order to evaluate the influence of hydroperoxides on the epoxidation rate, we incubated [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C]linoleic acid in the presence of PXG4 and the same concentration (200 lM) of cumene hydroperoxide, 13 HPOD and 13 HPOT as co-oxidants. Analysis of the products showed that the formation of the final product (i.e.…”

Section: Pxg4 Catalyzed Intermolecular and Intramolecular Transfer Ofmentioning

confidence: 99%

“…Found at high amounts in the seeds of some exotic plants, vernolic acid (12,13-epoxy-cis-9-octadecenoic acid) has several potential industrial applications. It is used, for example, in the production of plastics, adhesives, nylon and paints [9,10]. Considerable effort has therefore been devoted to the identification and expression of the genes controlling its biosynthesis in commercial oil crops.…”

Section: Introductionmentioning

confidence: 99%

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A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

et al. 2012

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In plants, epoxygenated fatty acids (EFAs) are constituents of oil seeds as well as defence molecules and components of biopolymers (cutin, suberin). While the pleiotropic biological activities of mammalian EFAs have been well documented, there is a paucity of information on the physiological relevance of plant EFAs and their biosynthesis. Potential candidates for EFA formation are caleosin-type peroxygenases which catalyze the epoxidation of unsaturated fatty acids in the presence of hydroperoxides as co-oxidants. However, the caleosins characterized so far, which are mostly localized in seeds, are poor epoxidases. In sharp contrast, quantitative RT-PCR analysis revealed that PXG4, a class II caleosin gene, is expressed in roots, stems, leaves and flowers of Arabidopsis. Expressed in yeast, PXG4 encodes a calcium-dependent membrane-associated hemoprotein able to catalyze typical peroxygenase reactions. Moreover, we show here that purified recombinant PXG4 is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. Physiological linoleic and linolenic acids proved to be the preferred substrates for PXG4; they are oxidized into the different positional isomers of the monoepoxides and into diepoxides. An important regioselectivity was observed; the C-12,13 double bond of these unsaturated fatty acids being the least favored unsaturation epoxidized by PXG4, linolenic acid preferentially yielded the 9,10-15,16-diepoxide. Remarkably, PXG4 catalyzes exclusively the formation of (R),(S)-epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. These findings pave the way for the study of the functional role of EFAs and caleosins in plants.

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Section: Pxg4 Is a Regioselective Peroxygenasementioning

confidence: 56%

Section: Pxg4 Catalyzed Intermolecular and Intramolecular Transfer Ofmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

et al. 2012

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“…For example, halogenated and nonhalogenated soybean oil-based polyols have been reported by treating epoxidized soybean oil (ESO) with hydrochloric acid, hydrobromic acid, methanol, or hydrogen. 10,12,13 Epoxide rings in epoxidized plant oils could also be partially opened by water in the presence of glacial acetic acid by heating to $75 C. 14,15 Such polyols prepared by ring-opening reaction possess hydroxyl groups mostly located in the middle of the fatty acid chains, and partial fatty acid chains, the portion of fatty acids between hydroxyl group and the chain end, form the pendant groups.…”

mentioning

confidence: 99%

A novel vegetable oil–lactate hybrid monomer for synthesis of high‐T_g polyurethanes

Miao

Zhang

et al. 2009

J. Polym. Sci. A Polym. Chem.

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“…Preparation of Bio-Based Di/Polyols. Generally, vegetable oilbased di/polyols possess a wide distribution of molecular weight, composition, and branching (13)(14)(15). These di/polyols are obtained by hydroformylation, epoxidation, and metathesis reactions of double bonds as well as by ester bond breaking reactions.…”

Section: Methodsmentioning

confidence: 99%

Bio‐Based Hyperbranched Polyurethane Nanocomposites

Karak

2015

Encyclopedia of Polymer Science and Technology

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BIO-BASED HYPERBRANCHED POLYURETHANE NANOCOMPOSITESadjusting the ratio of isocyanate (-NCO) to hydroxyl (-OH) functionality and the chemical composition in the final structure of the polyurethane, different types of polymeric products like thermosetting resin and elastomer as well as thermoplastic and fiber can be obtained (3). In all such polyurethanes, the main linkage, urethane (-NH-C(=O) -O-) is a unique combination of rigid amide (-NH-C=O), which has a tendency to donate proton, and a flexible ester (-O-C=O) group, which has a tendency to accept proton. Further flexibility arises from the flexible soft segment and long hydrocarbon part of fatty acid chains of the vegetable oil component present in the bio-based segmented polyurethanes. Moreover, they are biodegradable and biocompatible. All these unique features of bio-based polyurethanes widen their applications in the domains of coating, paint, adhesive, sealant, composite, biomaterial, smart material, and so on.Again, incorporation of branching in the polymer structure greatly influences the processing and properties of the branched polymer. Thus hyperbranched polymers are treated as macromolecules for 21st century. These hyperbranched polymers are one type of dendritic polymers ( Fig. 1), where the other type is a perfectly regular structure with a three-dimensional architecture, known as a dendrimer (4). However, hyperbranched polymers are preferred in most of the industrial applications over multistep laborious synthesized dendrimers because of easier and simpler one-step synthetic protocol of the former as they can accommodate some defects in their structures. Thus mass-scale industrial production at relatively low cost is possible for hyperbranched polymers like conventional linear polymers. However, hyperbranched polymers enjoy many advantages over linear polymers (Fig. 1). These include a unique three-dimensional structural architecture with dendritic, linear, and terminal units, the presence of a large number of freely exposed surface groups, low polydispersity index, low viscosity, high solubility, high compatibility with other materials, etc. Therefore, bio-based hyperbranched polyurethanes are preferred as superior materials over their conventional analogs for different advanced applications.However, "virginity is not a virtue" in case of polymer, whatsoever the structural architecture is! Thus bio-based hyperbranched polyurethanes also require to be adulterated by incorporation of appropriate additives or ingredients. It is pertinent to mention here that most of the vegetable oil-based hyperbranched polyurethanes do not have required mechanical strength and toughness, although they possess very good flexibility. In this vein, conventional filled and composite systems are widely used, although both the approaches suffer from serious drawbacks, as a huge amount of additive(s) is necessary to be incorporated to achieve the desired level of performance of the stated polyurethanes. Most importantly, the resultant products lost most of the central a...

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Synthesis, characterization, antibacterial and corrosion protective properties of epoxies, epoxy-polyols and epoxy-polyurethane coatings from linseed and Pongamia glabra seed oils

Cited by 110 publications

References 28 publications

A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

A novel vegetable oil–lactate hybrid monomer for synthesis of high‐T_g polyurethanes

Bio‐Based Hyperbranched Polyurethane Nanocomposites

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Synthesis, characterization, antibacterial and corrosion protective properties of epoxies, epoxy-polyols and epoxy-polyurethane coatings from linseed and Pongamia glabra seed oils

Cited by 110 publications

References 28 publications

A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

A non‐canonical caleosin from Arabidopsis efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

A novel vegetable oil–lactate hybrid monomer for synthesis of high‐Tg polyurethanes

Bio‐Based Hyperbranched Polyurethane Nanocomposites

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Product

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A novel vegetable oil–lactate hybrid monomer for synthesis of high‐T_g polyurethanes