Photolytic and free‐radical polymerization of monomethyl maleate esters of epoxidized plant oil triglycerides

Abstract

Epoxidized soybean oil (ESO) was reacted with monomethyl maleate with AMC‐2 catalyst. Monomethyl maleate was found to react with 65% of the available epoxy groups to give the monomethyl maleic esters of ESO (MESO). 1H‐NMR, 13C‐NMR, and IR spectra of the new derivative confirmed the proposed structure. The NMR spectra revealed that the average number of monomethyl maleate groups per triglyceride molecule was 2.6. MESO was photopolymerized with ultraviolet light and was free radically homopolymerized and copolymerized with styrene (STY), vinyl acetate (VA), and methylmethacrylate (MMA). MESO was also reacted with maleic anhydride at the newly formed hydroxyl groups to give maleinized MESO, (MESOMA), which now contained 4.9 maleate unsaturations per triglyceride. Dynamic mechanical analysis revealed the dynamic modulus for styrene copolymers of MESO and maleinized MESO as 105 and 140 MPa, respectively. Both of these plant oil derived monomers are good candidates for a practical and economical liquid molding resin. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 626–633, 2007

Chemoenzymatic synthesis of oleic acid‐based polyesters for use as highly stable biomaterials

“…[9][10][11] One effective way to prepare high-molecular-weight polymers containing lipids is to attach them to the backbone chains of vinyl polymers. [12][13][14][15][16] Carbon-carbon double bonds of unsaturated lipids are usual the sites for attachment of polymerizable functional groups. Vinyl monomers such as maleic acid, maleic anhydride, and acrylic acid have been successfully applied to modify unsaturated lipids and subsequently polymerized.…”

“…Vinyl monomers such as maleic acid, maleic anhydride, and acrylic acid have been successfully applied to modify unsaturated lipids and subsequently polymerized. [12][13][14][15][16] Polymers prepared through this approach are only partially biodegradable, as the backbone chain structures are the same as their petroleum counterparts. Alternatively, lipid polymers can also be formed through copolymerization of monoglyceride with diacids, anhydrides, or diisocyanates, 10 thus producing polymers have lipids in the backbone structure and making it possible for complete biodegradation.…”

Effects of different epoxidation methods of soybean oil on the characteristics of acrylated epoxidized soybean oil-co-poly(methyl methacrylate) copolymer

“…Although ESO-and AESO-based polymers seem to be environmentally friendly materials, the epoxidation process should be improved by using more green chemistry. This is because on an industrial scale, ESO is produced by an in situ epoxidation in the presence of a strong acid as a catalyst such as H 2 SO 4 and H 3 PO 4 . The drawbacks of this method are the corrosion of equipment due to the acidic solution and the product must be neutralized and purified.…”

Vegetable oil-based epoxies

“…This MESO is photo-polymerised with ultraviolet light and free radically homopolymerised and copolymerised with styrene, vinyl acetate and methylmethacrylate. 34 MESO may also be reacted with maleic anhydride at the newly formed hydroxyl groups to give maleinised MESO. Thus a large number of resinous systems may be made from the epoxidised oil.…”