Development of novel phosphorus‐containing epoxy resins from renewable resources

Lligadas, Gerard; Ronda, Juan C.; Galià, Marina; Cádiz, Virgínia

doi:10.1002/pola.21794

Cited by 81 publications

(53 citation statements)

References 35 publications

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“…The dehydrochlorination under alkaline conditions will hydrolyze ester groups of triglycerides, even at room temperature. A triglyceride with terminal epoxy has been synthesized from 10-undecenoic acid and successfully used in epoxy-amine curing [28,29], whereas 10-undecylenic acid, a derivative of castor oil, has only one terminal double bond so the epoxidized triglyceride ester of 10-undecylenic acid has a lower oxirane content compared to ESO. Largescale production also seems impractical [30].…”

Section: Introductionmentioning

confidence: 99%

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Wang¹,

Schuman²

2013

Express Polym. Lett.

153

118

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Abstract. Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been synthesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxidized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF 3 catalyst or anhydride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

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Section: Introductionmentioning

confidence: 99%

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Wang¹,

Schuman²

2013

Express Polym. Lett.

153

118

View full text Add to dashboard Cite

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“…Char formation on the surface of these materials upon burning forms the basis of this property. [106] 5.1.3 Micelle-catalyzed oligomerization of undecylenic acid and further derivatization UA dispersions were studied in order to unravel biological phenomena of chitosan, such as its hypolipedemic effect. Chitosan can flocculate or stabilize aqueous dispersions of UA, which has been studied in detail.…”

Section: Undecylenic Acid In Resinsmentioning

confidence: 99%

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

2009

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A lot of attention is currently being paid to the transition to a biobased economy. In this movement, most efforts concentrate on the development of bioenergy applications including bioethanol, biodiesel, thermochemical conversion of biomass, and others. However, in the energy sector other nonbiomass alternatives are known, whereas no valuable alternatives are available when thinking about chemical building blocks. Therefore, it is also essential to develop new routes for the synthesis of bio-based chemicals and materials derived thereof. Such intermediates can originate either from plants or from animals. Castor oil is a non-edible oil extracted from the seeds of the castor bean plant Ricinus communis (Euphorbiaceae), which grows in tropical and subtropical areas. Globally, around one million tons of castor seeds are produced every year, the leading producing areas being India, PR China, and Brazil.2 10-Undecenoic acid or undecylenic acid is a fatty acid derived from castor oil that, owing to its bifunctional nature, has many possibilities to develop sustainable applications.

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“…[12] Other major processes have involved the conversion of vegetable oils or fats into epoxidized vegetable oils (EVOs) [13,14] or polyols. [15] Epoxidized vegetable oils can be cationically polymerized by latent thermal catalysts [13,14] or cured by amines [16] or anhydrides [17] to produce thermosetting resins, whereas the polyols can react with diisocyanates to produce vegetable oil based polyurethane thermosets [18,19] or waterborne polyurethane dispersions. [20] A considerable amount of research has been devoted to the conversion of the polyols to vegetable oil based polyurethanes, and the synthesis and properties of these novel bio-based materials have been recently reviewed elsewhere.…”

Section: Introductionmentioning

confidence: 99%

Novel Polymeric Materials from Vegetable Oils and Vinyl Monomers: Preparation, Properties, and Applications

2009

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Veggie-based products: Vegetable-oil-based polymeric materials, prepared by free radical, cationic, and olefin metathesis polymerizations, range from soft rubbers to ductile or rigid plastics, and to high-performance biocomposites and nanocomposites. They display a wide range of thermophysical and mechanical properties and may find promising applications as alternatives to petroleum-based polymers.Vegetable oils are considered to be among the most promising renewable raw materials for polymers, because of their ready availability, inherent biodegradability, and their many versatile applications. Research on and development of vegetable oil based polymeric materials, including thermosetting resins, biocomposites, and nanocomposites, have attracted increasing attention in recent years. This Minireview focuses on the latest developments in the preparation, properties, and applications of vegetable oil based polymeric materials obtained by free radical, cationic, and olefin metathesis polymerizations. The novel vegetable oil based polymeric materials obtained range from soft rubbery materials to ductile or rigid plastics and to high-performance biocomposites and nanocomposites. These vegetable oil based polymeric materials display a wide range of thermophysical and mechanical properties and should find useful applications as alternatives to their petroleum-based counterparts.

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Development of novel phosphorus‐containing epoxy resins from renewable resources

Cited by 81 publications

References 35 publications

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

Novel Polymeric Materials from Vegetable Oils and Vinyl Monomers: Preparation, Properties, and Applications

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