Kinetics for chlorination of maleic anhydride grafted polypropylene

Preparation of Chlorinated maleic anhydride grafted polypropylene (Cl‐PP‐g‐MAH) by free radical process was carried out using carbon tetrachloride (CCl₄) as the solvent and benzoperoxide (BPO) as the initiator. Effects of reaction temperature, concentrations of PP‐g‐MAH and BPO on the rate of chlorination were studied. The experimental results showed the actual rate constant for chlorination of maleic anhydride grafted polypropylene followed the Arrhenius law and the total apparent activation energy was 19.7 kJ mol^?1. The kinetic model for chlorination of maleic anhydride grafted polypropylene was found to be R = K[BPO]^0.53[C]^0.93. The properties of chlorination of maleic anhydride grafted polypropylene were better than those of maleic anhydride grafted polypropylene. The products were characterized by Fourier transform infrared spectroscopy. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007     

Peroxide‐catalyzed swell grafting of maleic anhydride onto polypropylene

A new grafting method was developed to incorporate maleic anhydride directly onto solid‐state polypropylene powders. Maleic anhydride grafts altered the nonpolar characteristics of polypropylene so that much better mixing was achieved in blends and composites of polypropylene with many other polymers and fillers. Maleic anhydride was grafted onto polypropylene by the peroxide‐catalyzed swell grafting method, with a maximum extent of grafting of 4.60%. Fourier transform infrared spectroscopy, differential scanning calorimetry, thermogravimetric analysis, scanning electron microscopy, tensile testing, and impact testing were used to characterize the isotactic polypropylene (iPP), maleic anhydride grafted polypropylene (MAH‐g‐iPP), and (isotactic polypropylene)/(calcium carbonate) composites (iPP/CaCO₃). The crystallinity and heat of fusion of the MAH‐g‐iPP decreased as the extent of grafting increased. The mechanical properties of the CaCO₃ filled polypropylene were improved by adding MAH‐g‐iPP as a compatibilizing agent. The dispersion of the fillers in the polymer matrix and the adhesion between the CaCO₃ particles and the polymer matrix were improved by adding the compatibilizer.     

Multiwalled carbon nanotubes‐based polypropylene composites: Influence of interfacial interaction on the crystallization behavior of polypropylene

Composites of polypropylene (PP) and multi‐walled carbon nanotubes (MWCNTs) were prepared via melt‐mixing utilizing Li‐salt of 6‐amino heaxanoic acid (Li‐AHA) modified MWCNTs in the presence of a compatibilizer (polypropylene‐g‐maleic anhydride; PP‐g‐MA). Improved interaction between the anhydride group of PP‐g‐MA and the amine functionality of Li‐AHA was confirmed via FTIR and Raman spectroscopic analysis. A higher glass transition temperature (T_g) of the PP phase has been observed in these composites as compared to pristine MWCNTs‐based composites. The crystallization temperature (T_c) of the PP phase was increased as a function of pristine MWCNTs concentration in PP/MWCNTs composites indicating hetero‐nucleating action of MWCNTs. However, T_c value was decreased in the presence of Li‐AHA modified MWCNTs indicating the adsorbed Li‐AHA on the MWCNTs surface. Moreover, T_c value was higher in the presence of Li‐AHA modified MWCNTs with PP‐g‐MA as compared to that of without PP‐g‐MA, suggesting the desorbed Li‐AHA from the MWCNTs surface due to melt‐interfacial reaction. Further, MWCNTs were extracted by hot vacuum filtration technique from PP/MWCNTs composites containing Li‐AHA and PP‐g‐MA. The isothermal crystallization kinetics showed a variation in crystallization behavior of the PP phase in the corresponding composites as compared to the “extracted MWCNTs.” POLYM. ENG. SCI., 57:183–196, 2017. © 2016 Society of Plastics Engineers     

Modification of polypropylene via the free‐radical grafting ternary monomer in water suspension systems

Maleic anhydride, styrene, and butyl acrylate were grafted onto polypropylene (PP) via free‐radical polymerization. The grafted product, polypropylene‐g‐(maleic anhydride–styrene–butyl acrylate) (PP‐g‐PMSB), was prepared in a water suspension system, and a nongrafted polymer, poly(maleic anhydride–styrene–butyl acrylate) (PMSB′), was produced at the same time. The optimal synthesis conditions were determined by orthogonal experiments. The crystallinity, thermal stability, melt flow rate, and hydrophilicity of the grafting samples were investigated in the presence or absence of PMSB′. The results indicate that the grafting percentage (G_p) of PP‐g‐PMSB and the content of PMSB′ (C_m) increased as the monomer content increased under the optimum reaction conditions. All of these ternary monomers were grafted onto the PP backbone as long‐chain branches. With increasing G_p, PP‐g‐PMSB's polarity and thermal stability increased, the crystallinity decreased, and the molecular distribution became narrower. The contact angle decreased to 72.12° when G_p was 6.87%. With increasing C_m, the crystallinity and thermal stability of the grafting products decreased compared to PP‐g‐PMSB and the molecular distribution grew wider. The contact angle decreased to 63.51° when C_m was 3.64%; this indicated that the presence of PMSB′ further improved the hydrophilicity of the grafted products. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and characterization of high‐density polypropylene‐grafted polyethylene via a macromolecular reaction and its rheological behavior

High‐density polyethylene grafted isotactic polypropylene (PP‐g‐HDPE) was prepared by the imidization reaction between maleic anhydride grafted polyethylene and amine‐grafted polypropylene in a xylene solution. The branch density was adjusted by changes in the molar ratio between maleic anhydride and primary amine groups. Dynamic rheology tests were conducted to compare the rheological properties of linear polyolefins and long‐chain‐branched polyolefins. The effects of the density of long‐chain branches on the rheological properties were also investigated. It was found that long‐chain‐branched hybrid polyolefins had a higher storage modulus at a low frequency, a higher zero shear viscosity, a reduced phase angle, enhanced shear sensitivities, and a longer relaxation time. As the branch density was increased, the characteristics of the long‐chain‐branched structure became profounder. The flow activation energy of PP‐g‐HDPE was lower than that of neat maleic anhydride grafted polypropylene (PP‐g‐MAH) because of the lower flow activation energy of maleic anhydride grafted high‐density polyethylene (HDPE‐g‐MAH). However, the flow activation energy of PP‐g‐HDPE was higher than that of PP‐g‐MAH/HDPE‐g‐MAH blends because of the presence of long‐chain branches. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

The reaction of polypropylene with maleic anhydride

An addition reaction of maleic anhydride with polypropylene takes place in the presence of radical reagents or sunlight. The initial rate of the reaction was proportional to the concentration of polypropylene and maleic anhydride, and one-half power of the concentration of the radical reagents. The increase in the temperature from 80 to 120°C increased the rate of the reaction and di-cumyl peroxide was effective as a radical reagent for this reaction. Ionic crosslinked rubber-like polymers were obtained from the reaction of maleic polypropylene with some alkali metal compounds. They showed the characteristic absorption band due to ? COO^? in their infrared spectra.     

The effect of compatibilizers and organically modified nanoclay on the morphology and performance properties of poly(acrylonitrile–butadiene–styrene)/polypropylene blends

In this study, poly(acrylonitrile–butadiene–styrene)/polypropylene (ABS/PP) blends with various compositions were prepared by melt intercalation in a twin‐screw extruder. Modifications of the above blends were performed by using organically modified montmorillonite (OMMT, Cloisite 30B) reinforcement as well as two types of compatibilizers, namely polypropylene grafted with maleic anhydride (PP‐g‐MAH) and ABS grafted with maleic anhydride (ABS‐g‐MAH). Increasing the PP content in ABS matrix seems to increase the melt flow and thermal stability of their blends, whereas a deterioration of the tensile properties was recorded. On the other hand, the addition of ABS to PP promotes the formation of the β‐crystalline phase, which became maximum at 30 wt% ABS concentration, and increases the crystallization temperature (T_c) of PP. A tendency for increase of T_c was also recorded by incorporation of the above compatibilizers, whereas the glass transition temperature (T_g) of PP and SAN phase in ABS was reduced. Regarding the Young's modulus, the greatest improvement was observed in pure ABS/PP blends containing organically modified nanoclay. However, in reinforced pure PP, the use of compatibilizers is recommended in order to improve the elastic modulus. The addition of OMMT to noncompatibilized and compatibilized ABS/PP blends significantly improves their storage modulus. POLYM. ENG. SCI., 56:458–468, 2016. © 2016 Society of Plastics Engineers     

Crystallization behavior of polypropylene/polyamide 6/montmorillonite nanocomposites

Polymer blended materials such as polyamide 6 (PA6)/polypropylene (PP) blends have received considerable attention in recent years. To improve the compatibility of PA6 and PP, compatibilizers like maleic anhydride‐g‐polypropylene (MPP) are often added. In addition, organically modified montmorillonite (MMT) is also used to improve the properties of various materials. In this work, the crystallization behavior of PP/PA6/MMT nanocomposites with MPP compatibilizer was investigated systematically. The annealing process effectively improved the crystallization of α‐PP. The crystallization temperature (T_c) of PA6 was increased by ca 2–3 °C on introducing MPP or MMT alone to the PP/PA6 system, whereas T_c of PP underwent no obvious change. However, when MPP and MMT were added simultaneously, T_c of PP and PA6 increased by 6.6 and 4.2 °C, respectively, and a new crystallization peak corresponding to PP‐g‐PA6 copolymer phase was observed at 162.5 °C. The combined effect of MPP and MMT led to better compatibility of PP with PA6. Moreover, the results of a non‐isothermal crystallization kinetics experiment revealed that the simultaneous introduction of MPP and MMT markedly shortened the crystallization time. Copyright © 2010 Society of Chemical Industry     

Study on the microstructure and properties of bromobutyl rubber (BIIR)/polyamide‐12 (PA12) thermoplastic vulcanizates (TPVs)

In this study, polyamide‐12 (PA12)/brominated isobutylene‐isoprene (BIIR) TPVs with good mechanical properties and low gas permeability were prepared by dynamic vulcanization in a twin‐screw extruder. The effects of three kinds of compatibilizers on the microstructure and properties of BIIR/PA12 TPV were studied. The compatibility between BIIR and PA12 was improved when maleated hydrocarbon polymeric compatibilizer is added. The reaction between maleic anhydride and amine in polyamide leads to the in situ formation of hydrocarbon polymer grafted polyamide which subsequently can be used to lower the interfacial tension between BIIR and polyamide. The compatibilizing effect of maleic anhydride modified polypropylene (PP‐g‐MAH) on BIIR/PA12 blends is the best among these compatibilizers because the surface energy of PP‐g‐MAH is very close to that of BIIR. The dispersed rubber phase of the blend compatibilized by PP‐g‐MAH shows the smallest size and more uniform size distribution, and the resulting TPVs show the best mechanical properties. The effects of fillers on the properties of BIIR/PA12 TPV were also investigated. The size of the BIIR phase increases with the increase in the content of CaCO₃. The modulus and tensile strength of TPVs increased with the increase in the content of CaCO₃ because of the reinforcing effect of CaCO₃ on TPVs. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 43043.     

The Effect of Spray-Freeze Drying of Montmorillonite on the Morphology,Dispersion, and Crystallization in Polypropylene Nanocomposites

The spray-freeze drying (SFD) technique was applied to sonicated aqueous suspensions of spray-dried montmorillonite clay (MMT) to produce highly porous agglomerates (SFD-MMT). Both MMT (used as a reference) and SFD-MMT were subsequently incorporated in polypropylene (PP) via melt compounding to produce 2 wt % nanocomposites with and without maleic anhydride grafted polypropylene (PP-g-MA). Polypropylene nanocomposites containing SFD-MMT exhibited thinner silicate flake layers compared to large agglomerates in PP/MMT nanocomposites. SFD-MMT particles became even more finer in the presence of PP-g-MA (i.e., in PP/PP-g-MA /SFD-MMT) where it hindered PP crystallization instead of serving as nucleation sites for the PP crystallization during rapid cooling. SFD-MMT improved the thermal stability of PP/PP-g-MA by 30°C compared to only 5–8°C for MMT/nanocomposites. MMT acts as a heterogeneous nucleating agent in the nucleation-controlled PP nanocomposites, but the hindrance effect was observed for the PP/PP-g-MA with SFD-MMT. PP/PP-g-MA/SFD-MMT exhibited twice the edge surface energy as compared to PP/PP-g-MA/MMT. The incorporation of both types of MMT raised the tensile moduli of PP and PP/PP-g-MA, with no improvement in their tensile strength and a decrease in the elongation at break. The PP/PP-g-MA/SFD-MMT showed brittle failure. POLYM. ENG. SCI., 60:168–179, 2020. © 2019 Society of Plastics Engineers     

Polypropylene/silica nanocomposites prepared by in-situ melt ultrasonication

A novel process using ultrasonic irradiation to enhance nanosilica dispersion in polypropylene-based nanocomposites has been proposed and investigated. The nanocomposites were isotactic polypropylene reinforced with silica nanoparticles at 3 wt% loading level. Ultrasonic processing in the melt state is an effective method for improving nanosilica dispersion. The effectiveness of the proposed ultrasonic processing technique on polypropylene nanocomposites was evaluated by XRD and transmission electron microscopy (TEM). Poly(propylene-g-maleic anhydride) copolymer (PP-g-MAH) containing 5 wt% maleic anhydride content was added to nanocomposites at 0.5 wt% concentration based on silica content. PP-g-MAH plays an important role in nanosilica dispersion in polymer matrix and interface interaction. The reaction of maleic anhydride groups with the hydroxyl groups on the surface of nanosilica was characterized by FTIR spectrum. The final nanocomposites result in a further enhancement of mechanical properties because of silica agglomerate reduction and improving interface combination, even loading level being much lower than that of ordinary fillers in conventional composites. POLYM. COMPOS., 2009. © 2009 Society of Plastics Engineers     

Combination of double‐modified clay and polypropylene‐graft‐maleic anhydride for the simultaneously improved thermal and mechanical properties of polypropylene

Double‐modified montmorillonite (MMT) was first prepared by covalent modification of MMT with 3‐aminopropyltriethoxysilane and then intercalation modification by tributyl tetradecyl phosphonium ions. The obtained double‐modified MMT was melt compounded with polypropylene (PP) to obtain nanocomposites. The dispersion of the double‐modified MMT in PP was found to be greatly improved by the addition of PP‐graft‐maleic anhydride (PP‐g‐MA) as a “compatibilizer,” whose anhydride groups can react with the amino groups on the surface of the double‐modified MMT platelets and thus improve the dispersion of MMT in PP. Fourier transform infrared, X‐ray diffraction, transmission electron microscopy, thermogravimetric analysis, scanning electron microscopy, and tensile test were used to characterize the structure of the double‐modified MMT, morphology, and the thermal and mechanical properties of the nanocomposites. The results show that PP‐g‐MA promotes the formation of exfoliated/intercalated morphology and obviously increases the thermal properties, tensile strength, and Young's modulus of the PP/double‐modified MMT nanocomposites. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Effect of montmorillonoite modification and maleic anhydride‐grafted polypropylene on the microstructure and mechanical properties of polypropylene/montmorillonoite nanocomposites

Two types of modified montmorillonite (MMT) were achieved using octadecylamine as the modifying agent by the methods of dry process and wet route. Polypropylene (PP)/MMT nanocomposites were prepared using the melt mixing technique and employing maleic anhydride‐grafted polypropylene (PP‐MA) as the compatibilizer. The modification of montmorillonite was characterized by fourier transform infrared spectroscopy (FTIR), X‐ray diffraction (XRD), and scanning electron microscope (SEM). The effect of MMT modification and PP‐MA on the microstructure and properties of PP/MMT nanocomposites was investigated by SEM, differential scanning calorimeter (DSC), thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA), and polarizing microscopy. The results show that organic montmorillonite modified by wet process (WOMMT) has a large d‐spacing increment; whereas montmorillonite modified by dry process (DOMMT) shows little d‐spacing increment. Furthermore, the mechanical properties of composites incorporating WOMMT are better than that containing DOMMT. As a third component, the addition of PP‐MA benefits the formation of exfoliated structure and the dispersion of MMT in PP matrix, and hence, enhances the physical properties of the nanocomposite. With the presence of PP‐MA, the highly dispersed MMT increases the number of spherulite crystals, enhances the melting enthalpy, improves the thermal stability, and induces the desired tiny crazes more effectively. MMT increases the storage modulus (E′) and glass‐transition temperature (T_g) of PP because of the stiffness of MMT layers, but PP‐MA decreases them owing to its high melt flow index, both of which were in favor of improving the physical properties. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 3952–3960, 2013     

Phase morphology and interfacial characteristics of polycarbonate/acrylonitrile‐ethylene‐propylene‐diene‐styrene blends compatibilized by styrene‐maleic anhydride copolymers

Blends of polycarbonate (PC) and acrylonitrile ‐ ethylene‐propylene‐diene‐styrene (AES) were reactive compatibilized by styrene‐maleic anhydride copolymers (SMA). The changes in phase morphology and interfacial characteristics of the blends as a function of maleic anhydride content of SMA and the concentration of compatibilizer have been systematic studied. The occurrence of reaction between the terminal hydroxyl groups of PC and the maleic anhydride (MA) of compatibilizer was confirmed by fourier transform infrared (FTIR) spectroscopy. A glass transition temperature (T_g) with an intermediate value between T_g(AES) and T_g(PC) was found on differential scanning calorimeter (DSC) curves of PC/AES blends compatibilized with SMA contains high levels of MA. Furthermore, at lower compatibilizer content, increase of the compatibilizer level in blends result in decreasing gap between two T_gs corresponding to the constituent polymers. Small angle X‐ray scattering (SAXS) test results indicated that compatibilizer concentration for the minimum of blend interface layer's thickness was exactly the same as it was when compatibilized PC/AES blend exhibited optimal compatibility in DSC test. The observed morphological changes were consistent well with the DSC and SAXS test results. A new mechanism of interfacial structural development was proposed to explain unusual phenomena of SMA compatibilized PC/AES blends. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42103.     

Preparation of nonleaching antimicrobial polypropylene wax and its application in polypropylene

Antimicrobial polypropylene (PP) has been widely used. Its highly effective antimicrobial activities and nonleaching characteristics remain concerns. In this study, polypropylene wax (PPW) grafted with maleic anhydride was first prepared; this was followed by a melting reaction with polyhexamethylene guanidine hydrochloride (PHMG) to obtain antimicrobial PPW [polypropylene wax grafted with polyhexamethylene guanidine hydrochloride (PPW‐g‐PHMG)]. PPW‐g‐PHMG was then melt‐blended with PP to prepare antimicrobial PP. Fourier transform infrared spectra confirmed that PHMG was covalently bonded on the PPW chains, and transmission electron microscopy images showed a uniform distribution of PHMG in the PPW matrix. The resulting antimicrobial PP exhibited excellent antimicrobial activity against Escherichia coli. The ring‐diffusion test further disclosed its nonleaching characteristics. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 44190.     

Thermal evaluation of PHB/PP‐g‐MA blends and PHB/PP‐g‐MA/vermiculite bionanocomposites after biodegradation test

This study aimed to evaluate the thermal behavior of polyhydroxybutyrate (PHB)/polypropylene grafted with maleic anhydride (PP‐g‐MA) blends and PHB/PP‐g‐MA/vermiculite bionanocomposites submitted to the biodegradation test according to ASTM G 160‐03. The blends and bionanocomposites were prepared by melt intercalation method using a single screw extruder, and then, compression molded. The thermal analyzes were performed by thermogravimetry (TG) and differential scanning calorimetry. It was verified the decrease of onset degradation temperature and the melting temperature mainly after 86 days of exposure to the simulated soil. This behavior was more pronounced in bionanocomposites because of interactions between the maleic anhydride groups and the clay favoring biodegradation, making the systems more amorphous and propitious to the attack of microorganisms. POLYM. ENG. SCI., 56:555–560, 2016. © 2016 Society of Plastics Engineers     

Synthesis of polypropylene‐graft‐maleic anhydride compatibilizer and evaluation of nylon 6/polypropylene blend properties

Polymer blends based on polyolefins are of a great interest owing to their broad spectrum of properties and practical applications. However, because of poor compatibilities of components, most of these systems generally exhibit high interfacial tension, a low degree of dispersion and poor mechanical properties. It is generally accepted that polypropylene (PP) and nylon 6 (N6) are not compatible and that their blending results in poor materials. The compatibility can be improved by the addition of a compatibilizer, and in this study PP was functionalized by maleic anhydride (MAH) in the presence of an optimized amount of dicumyl peroxide (DCP). The reaction was carried out in the molten state using an internal mixer. Then, once the compatibilizer polypropylene‐graft‐maleic anhydride (PP‐g‐MAH) was prepared, it was added at various concentrations (2.5–10 wt%) to 30/70 glass fibre reinforced N6 (GFRN6) PP, and the mechanical properties were evaluated. It was found that the incorporation of the compatibilizer enhanced the tensile properties (tensile strength and modulus) as well as the Izod impact properties of the notched samples. This was attributed to better interfacial adhesion as evidenced by scanning electron microscopy (SEM). The optimum in these properties was achieved at a critical PP‐g‐MAH concentration. Copyright © 2005 Society of Chemical Industry     

Extrusion foaming behavior of a polypropylene/nanoclay microcellular foam

With maleic anhydride grafted polypropylene (PP‐g‐MAH) as a compatibilizer, composites of block‐copolymerized polypropylene (B‐PP)/nanoclay were prepared. The effects of the PP‐g‐MAH and nanoclay content on the crystallization and rheological properties of B‐PP were investigated. The microcellular foaming behavior of the B‐PP/nanoclay composite material was studied with a single‐screw extruder foaming system with supercritical (SC) carbon dioxide (CO₂) as the foaming agent. The experimental results show that the addition of nanoclay and PP‐g‐MAH decreased the melt strength and complex viscosity of B‐PP. When 3 wt % SC CO₂ was injected as the foaming agent for the extrusion foaming process, the introduction of nanoclay and PP‐g‐MAH significantly increased the expansion ratio of the obtained foamed samples as compared with that of the pure B‐PP matrix, lowered the die pressure, and increased the cell population density of the foamed samples to some extent. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 44094.     

Influence of the compatibilizer/nanoclay ratio on final properties of polypropylene matrix modified with montmorillonite-based organoclay

The use of nanoclays as additives for polymer matrices requires, in some cases (with non-polar matrices) the use of a compatibilizer agent which will act as a bridge or permanent buffer for nanoclay-matrix interaction. In this research, we have worked on the improvement of mechanical and thermal properties of polypropylene matrices by adding montmorillonite based nanoclays (MMT) which have been previously modified with an organic component (a quaternary ammonium salt modifier). In this particular case, we have worked on the optimization of the compatibilizer:nanoclay ratio. As a compatibilizer agent it has been used a propylene graft maleic anhydride copolymer (PP-g-MA) and the PP-g-MA:MMT ratio has varied from 0.25:1 to 4:1. Nanoclay dispersion and intercalation–exfoliation degree has been investigated by X-ray diffraction spectroscopy (XRD) and transmission electron microscopy (TEM). Also, mechanical and thermal properties for different PP-g-MA:MMT ratios have been determined. The results show optimum dispersion and intercalation–exfoliation levels for PP-g-MA:MMT ratios close to 3:1 and 4:1 and also we can observe a slight increase in mechanical and especially in thermal properties for similar ratios.     

Free radical meleation of soybean oil <Emphasis Type="Italic">via</Emphasis> a single-step process

In this study a new value-added product was developed from soybean oil for use as a chemical feedstock. The investigation and optimization of this work resulted in a fast and simple process to maleate soybean oil. An anhydride functionality was introduced into soybean oil through a free radical-initiated maleation. Two initiators were evaluated, 2,5-bis(tert-butylperoxy)2,5-dimethylhexane peroxide and di-tert-butyl peroxide. The effects of reaction time, initiator concentration, maleic anhydride concentration, and reaction temperature were investigated. The maleated soybean oil was characterized using acid value, iodine value, and FTIR spectroscopy. The acid value was directly related to the initial concentration of maleic anhydride, whereas the concentration and type of initiator had little effect on the acid value. The peroxide-initated functionalization of soybean oil with maleic anhydride in a closed vessel at elevated pressure and temperature was found to proceed by a Diels-Alder mechanism.