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Photolytic and free‐radical polymerization of monomethyl maleate esters of epoxidized plant oil triglycerides
Author(s) -
Esen Hüseyin,
Küsefoğlu Selim,
Wool Richard
Publication year - 2006
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.25155
Subject(s) - epoxidized soybean oil , copolymer , maleic anhydride , polymer chemistry , styrene , monomer , polymerization , vinyl acetate , chemistry , materials science , organic chemistry , polymer , raw material
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). 1 H‐NMR, 13 C‐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