Epoxidised triglycerides

Acrylated epoxidised soybean oil (AESO) (Rg. 7.6) is synthesised from the reaction of acrylic acid with epoxidised triglycerides. Similarly malein-ated hydroxylated soybean oil (Rg. 7.6) can be obtained by the reaction of epoxidised oil with maleic anhydride. 

Epoxidised triglycerides can be found in natural oils, such as vernonia plant oil, or they may be synthesised from more common unsaturated oils, such as soybean or hnseed oil, by a standard epoxidation reaction. The reaction of acrylic acid with epoxidised soybean oil (ESO) occurs through a standard substitution reaction. Although the reaction of ESO with acrylic acid is partially acid catalysed by the acrylic acid itself, tertiary amines such as A,A-dimethylanihne, triethylamine and 1, 4-diazobicyclo[2.2.2]-octane are commonly used as the catalysts. 

Photo-initiated cationic polymerisation of epoxidised oils has been the subject of intense scrutiny by the research team led by Crivello, starting with the groundbreaking study in 1992 [1-3] applied to several epoxidised triglycerides, with the linseed homologue shown in Scheme 4.1. Since that contribution, this [1-3] and other research teams have carried out further research, including use of thermally activated... 

A novel triglyceride-based a, p-unsaturated ketone, obtained by photoperoxidation from high oleic sunflower oil, can be cross-linked with diamino diphenyl methane through the aza-Michael addition reaction. The reaction of p-toluidine with either enone-containing methyl oleate or epoxidised methyl oleate, produces an alternative to amine-cured epoxidised vegetable oil thermosets. ... 

Environmentally friendly, bio-based flame retardant epoxy resins have been reported from a di-epoxy fatty compound, 10-[2, 5 -bis(9-oxiranyl-nonayloxy) phenyl]-9,10-dihydro-9-oxa-10-phosphaphenanthrene-l 0-oxide (Rg. 7.5a) and epoxidised 10-undecenoyl triglyceride and epoxidised methyl-3, 4, 5-tris(10-undecenoyloxy)benzoate (Hg. 7.5b and c). The limiting oxygen index (LOI) values of the cured products indicate good flame retardant behaviour owing to the formation of a protective phosphorous-rich layer which slows down degradation and protected the products. 

Conversion of internal unsaturations in triglycerides and their fatty acids into epoxide moieties has been optimised to enable their industrial implementation an economically viable operation with some oils. This strategy has opened the way to elaboration of macromolecular materials that could become real commodities. This rationale implies that the performance of these polymers should adequately match the respective applications they are conceived to fulfill. Apart from such common epoxidised oils, this section deals with other more elaborate monomers in which the oxirane function is present as an end group and hence more reactive. 

Incorporation of hydroxyl groups in triglycerides and their fatty acids constitutes a major research area, particularly within the broad context of the synthesis of biological-based PU. C=C unsaturations in plant oils can be modified by different chemical mechanisms to introduce -OH moieties (Scheme 4.8) [31]. One of the most representative approaches is opening the oxirane ring in epoxidised oils by various reagents (Scheme 4.10). 

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