Epoxidized soybean oil, ESO

The use of oleochemicals in polymers has a long tradition. One can differentiate between the use as polymer materials, such as linseed oil and soybean oil as drying oils, polymer stabilizers and additives, such as epoxidized soybean oil as plasticizer, and building blocks for polymers, such as dicarboxylic acids for polyesters or polyamides (Table 4.2) [7]. Considering the total market for polymers of ca. 150 million tonnes in 1997 the share of oleochemical based products is relatively small - or, in other terms, the potential for these products is very high. Without doubt there is still a trend in the use of naturally derived materials for polymer applications, especially in niche markets. As an example, the demand for linseed oil for the production of linoleum has increased from 10000 tonnes in 1975 to 50 000 tonnes in 1998 (coming from 120000 tonnes in 1960 ) [8a]. Epoxidized soybean oil (ESO) as a plastic additive has a relatively stable market of ca. 100000 tonnes year-1 [8b]. 

Fig. 10 Photocuring of a 1/1 blend of ELNR-70 and epoxidized soybean oil (ESO). Conversion of the epoxy ring of ELNR ( ) and of ESO (A).

Epoxy ester. Epoxy ester plasticizers have limited compatibility with PVC. Therefore, they are used at low levels. Epoxidized soybean oil (ESO), the most widely used epoxy plasticizer, is also used as a secondary heat stabilizer. As a plasticizer, it provides excellent resistance to extraction by soapy water and low migration into adjoining materials that tend to absorb plasticizers. Other epoxy plasticizers include epoxidized linseed oil and epoxidized tall oils. Tall oils are prepared from tall oil fatty acids and Cs-Cs alcohols. 

Other materials that are often referred to as secondary plasticizers include materials such as epoxidized soybean oil (ESO), epoxidized linseed oil (ELO), and epoxidized tallate oil (ETO). These act as secondary stabilizers because of their epoxy content by removing the HCI from the degrading polymer. The ETO provides the best low temperature properties of the epoxidized oils. 

Particularly, in the past decade, much effort has been dedicated to producing soybean oil-based polymeric materials. 3,4-Epoxidized soybean oil (ESO) is manufactured by the epoxidation of the double bonds of the SBO triglycerides with hydrogen peroxide, either in acetic acid or in formic acid, and it is industrially available in large volumes at a reasonable cost. 

Epoxidized soybean oil (ESO)/octadecyl-modified montmorillonite (OMM) Thermal latent catalyst + heat During thermal treatment, cross-linking occurs Additions of 5 and 15 wt% OMM show intercalated and randomly oriented structures in polymer matrices Increase in glass transition temperature (Tg) with increasing the clay content from 5 to 15 wt%, ranging from —2 to 4 °C. Uyama et al. (2003)... 

In similar conditions Rosu et al. [52] conducted controlled photo-aging experiments of chemically modified surface of Abies alba L. softwood species. Chemical modification was undertaken in two stages (Scheme 6—reproduced with kind permission from Elsevier— License No. 3723031483298). The former stage consisted in the reaction of wood components with succinic anhydride (SA) to yield monoester entities with final carboxyl groups, followed by crosslinking with epoxidized soybean oil (ESO) in the latter stage. Success of flie chemical modification reactions was confirmed by FTIR. 

Fluidized Bed-Coated Dishwasher Racks As these compounds may contain up to 25 phr of filler and pigment, and 50-60 phr of phthalate plasticizer (chosen for low odor and extractability), a resin of 0.85-0.95 IV is desirable. Nontoxic calcium/ zinc stabilizers are used, with 4-5 phr of epoxidized soybean oil (ESO) and 2-4 phr of a dispersion resin. 

---