Polymerization of maleic anhydride–modified plant oils with polyols

Abstract

ABSTRACT:In this study soybean oil triglycerides were reacted with maleic anhydride in an ene reaction to introduce more than two maleate residues per triglycerides. The maleinized soybean oil (SOMA) was then polymerized with diols to the half-ester stage only. Two different types of alcohols was used in this work: (1) short-chain polyhydroxy linear or cyclic alcohols having 2, 3, 4, or 6 hydroxyl groups; and (2) long-chain dihydroxy alcohols. The aim was to determine the effect of functionality and chain length by choosing alcohols with increasing number of hydroxyl groups and different chain lengths. The reaction of alcohols with anhydride functionalized soybean oil to give a polymeric halfester is a reaction that proceeds without the formation of byproducts and is different from complete polyesterification of maleinized oils, which are well known. To improve the reaction yields, different catalysts and different reaction conditions were examined. The structural analysis of the products was done with 1 H-NMR and IR spectroscopy. All of the new polymers obtained were resilient and soft rubbers at room temperature. Castor oil polymer mixed with 60% CaCO 3 and 12% cork powder gave a resilient and nontacky linoleum composition.

The effect of maleinized linseed oil as biobased plasticizer in poly(lactic acid)‐based formulations

“…reported a band located at 1708.5 cm −1 that corresponds to the carbonyl functional group. This peak can also be observed in the IR spectrum of MLO . Moreover, as pointed out by Balsamo et al .…”

Pressure-sensitive adhesives based on tung oil

“…In addition, the DA reaction used in this study to introduce anhydride groups onto tung oil for the preparation of TOMA proceeded at a much lower temperature of 100 °C than that (up to 230 °C) for the introduction of anhydride groups onto soybean or linseed oil via the "ene" reaction. 7,8 The reaction time of 1 h for the DA reaction was much shorter than that (at least 3 h) for the "ene" reaction. …”

“…It has been reported that polymerizations of maleinized soybean oil (MSO) containing more than two anhydride groups with di-or polyols such as ethylene glycol, glycerol, and poly(ethylene glycol) (PEG) with number-average molecular weights (M n ) of 160, 400 and 600 resulted in resilient and soft solids or sticky semisolids. 7 But none of these polymeric products was demonstrated to be suitable materials for PSA applications, which was most probably due to the chemical structures of the di-or polyols and/or MSO. In another study, long-chain hydroxyl-ended polyesters was prepared from polymerizations of dimerized fatty acids and fatty diols; the polyesters after being cured with maleic anhydride (MA)-modified soybean oil or linseed oil could result in PSAs.…”

Development of biobased polyurethane‐imides from maleinized cottonseed oil and castor oil

“…Maleinization is a grafting reaction of maleic anhydride (MA) on vegetable oils (VOs) that proceeds mainly by three mechanisms, namely, “ene” reaction or allylic addition, Diels‐Alder addition, and free radical copolymerization . The maleinization reaction through “ene” reaction path requires approximately 200°C to 230°C and resulting in the grafting of a succinic anhydride group to the allylic position of the triglyceride chain . These maleinized VOs (MVOs) with anhydride groups have applications in paints, binders, plasticizers, and UV‐curable coatings .…”