Vegetable oils epoxidation

The epoxidation of vegetable oil triglycerides is a well-known technology. Epoxidized vegetable oils found use in other industrial applications before their... 

Epoxidized Tall Oil, Octyl Ester Epoxidized Vegetable Oils... 

Epichlorohydrin Epoxidized Vegetable Oils Epoxidized Vegetable Oils Octyl Epoxy Tallate Epoxidized Vegetable Oils Butylene Oxide Ethylene Oxide Propylene Oxide Sodium Nitrite Copper Chloride Trichloiofluoromethane Dichlordifluoromethane Monochlorodifluoromediane Nitrobenzene Acetaldehyde Ethane... 

SCHEME 4.6 Partial carbonation of epoxidized vegetable oil. (Reprinted from O. Figovsky, L. Shapovalov, A. Leykin, O. Birukova, and R. Potesshnikova, Nonisocyanate Polyurethanes Based on Cyclic Carbonates and Nanostructures Composites, J. Scientific Israel Technology Advanced 14, no. 4 (2012) 95-106. With permission.)... 

The major market for plasticizers is dominated by ptimary plasticizers, phthalate esters, while 10—15% of plasticizers are derived from vegetable oils. The annual plasticizer market is "0.91 MMT (1 million t) and growing. Of the epoxidized vegetable oils, soybean oil is used in "75% of production. Epoxy linseed oil is used in vinyl liners of botde caps and medical mbing, where extraction of plasticizet must be avoided. Epoxy sunflower oil is more compatible with vinyl resin, while epoxy tall oils are used in some plastic products. 

Other elastomers tested for toughening epoxies include polymethylmethacrylate grafted natural rubber (33). Chloroprene rubber and epoxidized vegetable oils. The latter have been found to have better toughness, lower water absorption and a potentially lower price than the unmodified epoxies. 

P. Muturi, D. Wang and S. Dirlikov, Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils . Prog Org Coat, 1994,25,85-94. 

F. L. Jin and S. J. Park, Thermomechanical behavior of epoxy resins modified with epoxidized vegetable oils , Polym Int, 2008,57,577-83. 

A plasticizer and a compatibilizer are used. As a plasticizer, an epoxidized vegetable oil or esterified and epoxidized vegetable oil is used an amount of 10-50%. Very effective is acetyl tributyl citrate. 

The viscosity of the epoxide prepolymers in many instances is reduced by additions of thin liquid epoxy compounds fliat may include cycloaliphatic epoxides or lactones. Various epoxidized vegetable oils, like epoxidized linseed, sunflower, soybean, and others are also used in some formulations. Table 3.4. lists come cycloaliphatic epoxy monomers used for such purposes. Vinyl ethers polymerize at a faster rate than do cycloaliphatic epoxides. They are, therefore, included in some formulations. Other materials fliat are included for such purposes or to control viscosity can be epoxy novolacs, glycidyl ethers of long chain alcohols. To control viscosity, polyols might also be used, because it is assumed that hydroxy group bearing compounds crosslink with the epoxy resins. 

Besides oxetanes, oxirane compounds have also been proposed as curable moieties (39). Examples of epoxidized vegetable oils having an unsaturated bond are olive oil, safflower oil, sunflower oil, soybean oil, and linseed oil. 

Plasticizers, which are added to improve the flexibility, softness and processibility of plastics, constitute a broad range of chemically and thermally stable products of a variety of chemical classes. Their principal use is in thermoplastic resins, and 80-85% of the world s production of plasticizers are used in polyvinyl chloride (PVC) manufacturing. Approximately 450 plasticizers are commercially available. Many are esters of carboxylic acids (e.g. phthalic, isophthalic, adipic, benzoic, abietic, trimellitic, oleic, sebacic acids) or phosphoric acid. Other plasticizers are chlorinated paraffins, epoxidized vegetable oils and adipate polymers. 

The authors would like to acknowledge the contributions of Robert F. Eaton of the Dow Chemical Co. in Bound Brook, N.J., who contributed to the sections on cycloaliphatic epoxies and epoxidized vegetable oils and the cationic curing mechanism. We also would like to thank Timothy Takas of Reichhold who kindly reviewed the article. We are indebted to many colleagues in the Epoxy Products and Intermediates business at Dow Chemical for their assistance in many ways to make this article possible. 

Another class of important renewable resources is represented by triglyceride plant oils. Among these vegetable oils, palm oil, soybean oil, rapeseed oil and sunflower oil are the four most important vegetable oils worldwide, holding a share of more than 80% of the market (Tan and Chow, 2010). Linseed oil and soybean oil are found to be the most popular epoxidized vegetable oils utilized today, since most of the potential vegetable oils are not available or their price is exorbitant. 

Natural polysaccharides, such as starch derived from com, wheat, rice or potato, and cellulose and its derivatives, are the main biopolymers employed in the development of green nanocomposites. The biodegradable thermoplastic polyester PLA, starch, and epoxidized vegetable oils are other examples of polymers widely used in the development of reinforced biopolymers. 

---