Hydrophobically modified poly[(divinyl ether)‐co‐(maleic anhydride)]: interactions with cyclodextrin derivatives and hydrogel formation

Hydrolyzed cyclocopolymer prepared from divinyl ether and maleic anhydride, poly[(divinyl ether)‐ co ‐(maleic anhydride)] (DIVEMA), was functionalized with aminoadamantane and subsequently compared with the hydrolyzed DIVEMA with respect to physicochemical properties. The complexation behavior of adamantyl modified DIVEMA with cyclodextrin derivatives was examined by dynamic light scattering, nuclear magnetic resonance spectroscopy and zeta potential. The scattering studies indicated the formation of well‐defined aggregated structures with an average diameter of 120 nm. These aggregated structures collapsed on addition of randomly methylated β‐cyclodextrin to give 4.2 nm in hydrodynamic diameter. Interactions with crosslinked β‐cyclodextrins indicated gel formation which was analyzed by means of rheology and temperature‐dependent viscosity showing disaggregation of the host‐guest system at 42 °C. This novel physical hydrogel is very interesting for medical applications as a drug delivery system with included anti‐tumor activity. Copyright © 2012 Society of Chemical Industry     

Synthesis and antitumor activity of poly(3,4‐dihydro‐2H‐pyran‐co‐maleic anhydride‐co‐vinyl acetate)

The radical‐initiated terpolymerization of 3,4‐dihydro‐2H‐pyran (DHP), maleic anhydride (MA), and vinyl acetate (VA), which were used as a donor–acceptor–donor system, was carried out in methyl ethyl ketone in the presence of 2,2′‐azobisisobutyronitrile as an initiator at 65°C in a nitrogen atmosphere. The synthesis and characterization of binary and ternary copolymers, some kinetic parameters of terpolymerization, the terpolymer‐composition/thermal‐behavior relationship, and the antitumor activity of the synthesized polymers were examined. The polymerization of the DHP–MA–VA monomer system predominantly proceeded by the alternating terpolymerization mechanism. The in vitro cytotoxicities of poly(3,4‐dihydro‐2H‐pyran‐alt‐maleic anhydride) [poly(DHP‐alt‐MA)] and poly(3,4‐dihydro‐2H‐pyran‐co‐maleic anhydride‐co‐vinyl acetate) [poly(DHP‐co‐MA‐co‐VA)] were evaluated with Raji cells (human Burkitt lymphoma cell line). The antitumor activity of the prepared anion‐active poly(DHP‐alt‐MA) and poly(DHP‐co‐MA‐co‐VA) polymers were studied with methyl–thiazol–tetrazolium testing, and the 50% cytotoxic dose was calculated. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 96: 2352–2359, 2005     

Synthesis of a novel linear water‐soluble β‐cyclodextrin polymer

A novel linear water‐soluble β‐cyclodextrin polymer has been prepared by grafting β‐cyclodextrin on poly[(methyl vinyl ether)‐alt‐(maleic anhydride)]. First, lithium hydride was used to obtain the mono‐alkoxide β‐CD. Grafting of β‐CD derivatives to the polymer backbone was then carried out by an esterification method. Using this method, polymers containing various amounts of β‐CD were synthesized. The resulting grafted polymers were characterized by two complementary methods, ¹H NMR and IR spectroscopy. The first was used to calculate the degree of substitution for the low amounts of β‐CD. The second method was very useful to evaluate the degree of substitution and the molar ratio of CD especially for high amounts of grafting. Our results indicate good agreement between both methods for intermediate rates. Copyright © 2004 Society of Chemical Industry     

Poly(ethylene‐alt‐maleic acid) as complexing reagent to separate metal ions using membrane filtration

Commercial, water‐soluble poly(ethylene‐alt‐maleic anhydride), P(E‐alt‐MAn), was quantitatively hydrolyzed by 0.2M NaOH to yield poly(ethylene‐alt‐maleic acid), P(E‐alt‐MAc). The polymer structure is confirmed by FT‐IR spectroscopy. As the pH increases, metal ion affinity increases because the majority of the functional groups are present as carboxylate anions, which can form more stable complexes at a higher pH. By increasing the filtration factor, Z, metal ion affinity does not significantly decrease, which means that the ligand–metal interaction is strong and cannot be destroyed by washing with water at the filtration cell's pH. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 2057–2061, 2006     

Effect of pH on the drug release rate from a new polymer–drug conjugate system

The corresponding N‐hydroximide and N‐methyl‐N‐hydroximide of poly[ethylene‐alt‐(maleic anhydride)] (weight average molecular weight (M_w) of 100–500 g mol^?1) were prepared as a new oral drug delivery system. Syntheses of N‐hydroximide and N‐methylhydroxamic acid of poly[ethylene‐alt‐(maleic anhydride)] were carried out by chemical modification of polymer with hydroxylamine and N‐methylhydroxylamine, respectively, to give water‐soluble polymers. These activated polymers were immobilized with ketoprofen in the presence of dicyclohexylcarbodiimide to give the corresponding water‐insoluble ketoprofen conjugates. All products were characterized by elemental analysis as well as Fourier transform infrared and ¹H NMR spectra. In vitro release of ketoprofen was studied by measuring UV absorption at λ_max = 260 nm as a function of time. This study demonstrated the potential use of N‐hydroximide and N‐methyl‐N‐hydroxamic acid of poly[ethylene‐alt‐(maleic anhydride)] as a drug delivery system. Controlled release was studied at different pH values and at different temperatures. At physiological temperature, the amount of drug released increased with increasing pH. The copolymer‐drug adducts released the drug very slowly at the low pH found in the stomach thus protecting the drug from the action of high acid conditions and resident digestive enzymes. These N‐hydroxamic acid polymer‐drug conjugates were found to be potentially useful in the delivery of macromolecular drugs to targeted sites in the lower gastrointestinal tract and the colon area. Copyright © 2007 Society of Chemical Industry     

Highly porous starch/poly(ethylene‐alt‐maleic anhydride) composite nanofiber mesh

In this study, starch‐based hybrid electrospun nanofiber meshes were fabricated by electrospinning. Spinning solutions were prepared by mixing starch and certain amounts of poly(ethylene‐alt‐maleic anhydride). Starch‐based nanofiber meshes became insoluble in water with thermal‐induced esterification of hydroxyl groups onto starch backbone. Morphologic and structure analysis of the electrospun nanofiber meshes were investigated by scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) techniques. Thermal properties of nanofiber meshes were characterized by thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC). Thermal stability of nanofiber meshes were increased with formation of intermolecular bonds between starch and poly(ethylene‐alt‐maleic anhydride). POLYM. COMPOS. 34:1321–1324, 2013. © 2013 Society of Plastics Engineers     

Novel colloidal nanofiber electrolytes from PVA‐organoclay/poly(MA‐alt‐MVE), and their NaOH and Ag‐carrying polymer complexes

Novel multifunctional polymer nanofiber electrolytes with covalence crosslinked structures from various solution blends of reactive intercalated poly(vinyl alcohol)/octadecylamine montmorillonite (as a matrix polymer), poly(maleic anhydride‐alt‐methyl vinyl ether) (as a partner polymer) and their NaOH‐absorbing and Ag‐carrying polymer complexes were fabricated via electrospinning. Chemical, physical, morphological, and electrical properties of nanofiber structures were investigated by FTIR, XRD, SEM, and electrical analysis methods. Ag precursors in fiber composites significantly improved phase separation processing, fiber morphologies, diameter distributions, and electrical properties of the fibers. In situ generation of Ag nanoparticles and their distribution on nanofiber surfaces during fiber formation occurred via complex formation between silver cations and electronegative functional groups from both matrix and partner polymers as stabilizing/reducing agents. Electrical resistance and conductivity strongly depended on matrix/partner polymer ratios and absorption time of NaOH solution on nanofibers. Addition of NaOH changed the electrical properties of fiber structures from almost dielectric state to excellent conductivity form. The fabricated unique nanofiber electrolytes are promising candidates for applications in power and fuel cell nanotechnology, electrochemical, and bioengineering processes as reactive semiconductive platforms. POLYM. ENG. SCI., 56:204–213, 2016. © 2015 Society of Plastics Engineers     

Novel conducting nanocomposite based on polypyrrole and modified poly(styrene‐alt‐maleic anhydride) via emulsion polymerization: Synthesis,Characterization, Antioxidant,and heavy metal sorbent activity

Novel polypyrrole/modified poly(styrene‐alt‐maleic anhydride) conducting nanocomposites were prepared via emulsion polymerization using sodium dodecyl sulfate as an emulsifier and ammonium persulfate as an oxidant. Modified poly(styrene‐alt‐maleic anhydride) was used as an external dopant for conductivity enhancement of polypyrrole. The conductivity of nanocomposites was measured with a four‐probe method. The maximum electrical conductivity of the nanocomposite was 1.40 S/cm. The data from this research showed that the novel nanocomposite presents good tendency for the removal of heavy metal ions from aqueous solutions. Also the prepared nanocomposites were analyzed for their antioxidant activity using 2,2‐diphenyl‐1‐picrylhydrazyl assay. The results showed that the antioxidant activity of the nanocomposite was 60%. The nanocomposites were characterized by Fourier transform infrared, ultraviolet–visible, X‐ray diffraction, field emission scanning electron microscopy, and differential scanning calorimetry measurements. POLYM. COMPOS., 36:138–144, 2015. © 2014 Society of Plastics Engineers     

Thermal properties of poly(maleic anhydride‐alt‐acrylic acid) in the presence of certain metal chlorides

Polychelates were synthesized by the addition of aqueous solutions of copper(II), cadmium(II), and nickel(II) chlorides to aqueous solutions of poly(maleic anhydride‐alt‐acrylic acid) [poly(MA‐alt‐AA)] in different pH media. The thermal properties of poly(MA‐alt‐AA) and its metal complexes were investigated with thermogravimetry and differential scanning calorimetry (DSC) measurements. The polychelates showed higher thermal stability than poly(MA‐alt‐AA). The thermogravimetry of the polymer–metal complexes revealed variations of the thermal stability by complexation with metal ions. The relative thermal stabilities of the systems under investigation were as follows: poly(MA‐alt‐AA)–Cd(II) > poly(MA‐alt‐AA)–Cu(II) > poly(MA‐alt‐AA)–Ni(II) > poly(MA‐alt‐AA). The effects of pH on the complexation and gravimetric analysis of the polychelates were also studied. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 3926–3930, 2006     

Bulk grafting of poly(styrene‐alt‐maleic anhydride) onto preirradiated polyolefin membranes in supercritical carbon dioxide

To take advantage of the property of supercritical carbon dioxide as both a solvent and swelling agent, the bulk grafting of poly(styrene‐alt‐maleic anhydride) [P(MAH‐alt‐St)] onto preirradiated polyolefin membranes was performed by a combination of γ‐ray‐preirradiation‐induced graft copolymerization and supercritical fluid‐swollen polymerization. The trapped radicals on the polyolefin backbones were uniformly distributed by γ‐ray irradiation under a nitrogen atmosphere. Subsequently, these polymeric trapped radicals initiated the alternating copolymerization of styrene (St) and maleic anhydride (MAH) infused into the swollen polymer matrix with the aid of supercritical CO₂. It was important that the graft copolymers were relatively pure without any contaminants, including homopolymers, monomers, and initiators. The experimental results show that the degree of grafting could be easily controlled. In addition, St/MAH could synergistically promote the bulk grafting process and strongly effect on the alternating trend; this was confirmed by element analysis and differential scanning calorimetry. Soxhlet extraction, X‐ray diffraction, and Fourier transform infrared spectroscopy indicated that the P(MAH‐alt‐St) was covalently bonded to the polymeric backbones. Scanning electron microscopy showed that the alternating graft chains were uniformly dispersed throughout the 5‐mm thickness of the polymer membranes on the nanometer scale. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Effect of cross‐linker on morphology,catalytic activity,and recyclability of immobilized palladium chloride

Two kinds of immobilized palladium (Pd) catalysts were prepared by reversible addition fragmentation chain transfer polymerization of pyridine‐containing monomer followed by immobilizing palladium chloride (PdCl₂) on block copolymers. Namely, one of them includes the cross‐linking structure of maleic anhydride with 1,6‐diaminohexane (cross‐linker), polystyrene‐block‐poly(4‐(4‐vinylbenzyloxy)butylpicolinate‐alt‐maleic anhydride)‐Pd (PS‐b‐P(VBP‐alt‐MAn)‐Pd), and the other is its non‐cross‐linking counterpart, polystyrene‐block‐poly(4‐(4‐vinylbenzyloxy) butylpicolinate)‐Pd (PS‐b‐PVBP‐Pd). From transmission electron microscopy images, it could be observed that they both assembled into micelles in the selective solvents. The Pd of PS‐b‐P(VBP‐alt‐MAn)‐Pd located in the core of micelles, whereas the Pd of PS‐b‐PVBP‐Pd was on the shell of the micelles. The PS‐b‐P(VBP‐alt‐MAn)‐Pd can be continuously used for five times without any appreciable loss of activity in the aqueous Suzuki‐coupling reaction. However, the catalytic activities of the PS‐b‐PVBP‐Pd decreased sharply with the increase in the recycle times. Thus, this promising cross‐linking strategy not only greatly restrained the loss of Pd in the catalytic cycles, but also effectively maintained the immobilized Pd catalyst's high activity. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Monolith‐ and Silica‐Supported Carboxylate‐Based Grubbs–Herrmann‐Type Metathesis Catalysts

The synthesis of silica‐ and monolith‐supported Grubbs–Herrmann‐type catalysts is described. Two polymerizable, carboxylate‐containing ligands, exo, exo‐7‐oxanorborn‐2‐ene‐5,6‐dicarboxylic anhydride and 7‐oxanorborn‐2‐ene‐5‐carboxylic acid were surface‐immobilized onto silica‐ and ring‐opening metathesis (ROMP‐) derived monolithic supports using “grafting‐from” techniques. The “1^st generation Grubbs catalyst”, RuCl₂(CHPh)(PCy₃)₂, was used for these purposes. In addition, a poly(norborn‐2‐ene‐b‐exo, exo‐norborn‐2‐ene‐5,6‐dicarboxylic anhydride)‐coated silica 60 was prepared. The polymer supported anhydride and carboxylate groups were converted into the corresponding mono‐ and disilver salts, respectively, and reacted with the Grubbs–Herrmann catalyst RuCl₂(CHPh)(IMesH₂)(PCy₃) [IMesH₂=1,3‐bis(2,4,6‐trimethylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene]. Heterogenization was accomplished by exchange of one chlorine ligand with the polymeric, immobilized silver carboxylates to yield monolith‐supported catalysts 4, 5 , and 6 as well as silica‐supported systems 7, 8 and 9 . The actual composition of these heterogenized catalysts was proven by the synthesis of a homogeneous analogue, RuCl[7‐oxanorbornan‐2‐(COOAg)‐3‐COO](CHPh)(IMesH₂)(PCy₃) ( 3 ). All homogeneous and heterogeneous catalysts were used in ring‐closing metathesis (RCM) of diethyl diallylmalonate, 1,7‐octadiene, diallyldiphenylsilane, methyl trans‐3‐pentenoate, diallyl ether, N,N‐diallyltrifluoracetamide and t‐butyl N,N‐diallylcarbamate allowing turnover numbers (TON's) close to 1000. In a flow‐through set‐up, an auxiliary effect of pendant silver carboxylates was observed with catalyst 5 , where the silver moiety functions as a (reversible) phosphine scavenger that both accelerates initiation and stabilizes the catalyst by preventing phosphine elution. Detailed catalytic studies were carried out with the monolith‐supported systems 4 and 6 in order to investigate the effects of temperature and chain‐transfer agents (CTA's) such as cis‐1,4‐diacetoxybut‐2‐ene. In all RCM experiments Ru‐leaching was low, resulting in a Ru‐content of the RCM products ≤3.5 μg/g (3.5 ppm).     

Preparation and characterization of a novel responsive hydrogel with a β‐cyclodextrin‐based macromonomer

Based on a combination of poly(N‐isopropylacrylamide), which could respond to an external temperature, and β‐cyclodextrin (β‐CD), which could form a molecular inclusion complex, a novel hydrogel, having both thermal and pH sensitivities and containing β‐CD and N‐isopropylacrylamide (NIPA) segments, was synthesized. For the incorporation of β‐CD into the polymer network, a macromonomer was prepared first by the reaction of a β‐CD‐based polymer with maleic anhydride in dimethylformamide and then by copolymerization with NIPA in an aqueous solution. Elemental analysis, IR spectroscopy, differential scanning calorimetry, and swelling measurements were employed for the characterization of the hydrogel chain structure and its physical properties. With methyl orange as a model compound in inclusion tests, it was found that the hydrogel not only possessed a remarkable supramolecular inclusion ability (with respect to that of the small molecule cyclodextrin) but also could sensitively respond to various external stimuli, including the temperature, pH, and ionic strength. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 361–367, 2003     

New polymers from plant oil derivatives and styrene‐maleic anhydride copolymers

In this study, styrene maleic anhydride copolymer (SMA2000, Styrene : Maleic Anhydride 2 : 1) is grafted and/or crosslinked with epoxidized methyl oleate, epoxidized soybean oil, methyl ricinoleate (MR), castor oil (CO), and soybean oil diglyceride. Base catalyzed epoxy‐anhydride and alcohol‐anhydride polyesters were synthesized by using the anhydride on SMA, the epoxy or secondary alcohol groups on the triglyceride based monomers. The characterizations of the products were done by DMA, TGA, and IR spectroscopy. SMA‐epoxidized soy oil and SMA‐CO polymers are crosslinked rigid infusible polymers. SMA‐epoxidized soy oil and SMA‐CO showed T_g's at 70 and 66°C, respectively. Dynamic moduli of the two polymers were 11.73 and 3.34 Mpa respectively. SMA‐epoxidized methyl oleate, poly[styrene‐co‐(maleic anhydride)]‐graft‐(methyl ricinoleate), and SMA‐soy oil diglyceride polymers were soluble and thermoplastic polymers and were characterized by TGA, GPC, DSC, NMR, and IR spectroscopy. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

The synthesis of symmetrical and unsymmetrical alkylaminonaphthalic‐1,8‐N‐alkylimides

Symmetrical 4‐n‐alkylamino and 2‐(n‐alkylamino)naphthalic‐1,8‐N‐alkylimides are prepared with primary amines from 4‐ and 2‐halogenonaphthalic‐1,8‐anhydrides in N‐methylpyrrolidinone. 3‐Halogenonaphthalic‐1,8‐anhydrides only react at the anhydride. Unsymmetrical 4‐compounds result by reaction of primary amines with the anhydride in ethanol and then the 4‐halogeno‐N‐alkyl product in N‐methylpyrrolidinone with primary or secondary amines © 2000 Society of Chemical Industry     

Synthesis of charged linear and crosslinked maleic diester polymers with electron‐beam irradiation

Series of maleic mono‐ and diester monomers have been prepared by esterification of maleic anhydride with poly(ethylene glycol) having different molecular weights, and with n‐dodecyl alcohol. These monomers were copolymerized with 2‐acrylamido‐2‐methylpropane sulfonic acid (AMPS) using different dose rates of electron‐beam irradiation ranging from 40 to 150 kGy. The synthesized copolymers were characterized by IR and ¹H NMR analysis. Their aggregation behaviour and viscometric properties in aqueous solutions were investigated. The crosslinked copolymers were prepared in aqueous acidic solutions at pH 1 or in the presence of 1% of N,N‐methylene bisacrylamide (MBA) as crosslinking agent. The final equilibrium water content and swelling capacities for the prepared hydrogels were determined in aqueous solutions at pH = 1, 6.8 and 12 at 298 K. Swelling equilibria for the prepared hydrogels were carried out in aqueous solutions of NaCl, KCl, CaCl₂, Na₂SO₄, K₂SO₄ and CaSO₄ at concentrations ranging from 1 × 10^?6 to 2 M at 298 K. © 2003 Society of Chemical Industry     

Variations of the glass‐transition temperature in the imidization of poly(styrene‐co‐maleic anhydride)

The imidization of poly(styrene‐co‐maleic anhydride) (SMA) was conducted, and the glass‐transition temperatures (T_g's) of the resulting products were measured with differential scanning calorimetry. The contributions from functional groups of maleic anhydride, N‐phenylmaleamic acid, and N‐phenylmaleimide to T_g were examined. T_g increased in the order of SMA < styrene–N‐phenyl maleimide copolymer < styrene–N‐phenyl maleamic acid copolymer and followed the Fox equation. T_g of the imidized products of SMA could be controlled by the conversions of both ring‐opening and ring‐closing reactions. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 2418–2422, 2007     

Antimicrobial poly(N‐vinyl‐2‐pyrrolidone‐alt‐maleic anhydride)/poly(ethylene imine) macrocomplexes

The antimicrobial polymer/polymer macrocomplexes were synthesized by radical alternating copolymerization of N‐vinyl‐2‐pyrrolidone with maleic anhydride [poly(VP‐alt‐MA)] with 2,2′‐azobis‐isobutyronitrile as an initiator at 65°C in dioxane solutions under nitrogen atmosphere, and interaction of prepared copolymer with poly(ethylene imine) (PEI) in aqueous solutions. The susceptibility of some Gram‐negative (Salmonella enteritidis and Escherichia coli) and Gram‐positive (Staphylococcus aureus and Listeria monocytogenes) bacteria to the alternating copolymer and its PEI macrocomplexes with different compositions in microbiological medium was studied using pour‐plate technique. All the studied polymers, containing biologically active moieties in the form of ionized cyclic amide, and macrobranched aliphatic amine groups and acid/amine complexed fragments, were more effective against L. monocytogenes than those for Gram‐positive S. aureus bacterium. This fact was explained by different surface layer structural architectures of biomacromolecules of tested bacteria. The resulting polymeric antimicrobial materials are expected to be used in various areas of medicine and food industry. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102:5841–5847, 2006     

Antibacterial activity and cytotoxicity of hydrogel–nanosilver composites based on copolymers from 2‐acrylamido‐2‐methylpropanesulfonate sodium

In this research, we contributed to the search for potential hydrogel–silver dressings by generating hydrogel–silver nanoparticles (AgNPs) composites prepared by the dipping of the crosslinked hydrogel poly(N‐vinylpyrrolidone‐co‐2‐acrylamido‐2‐methylpropanesulfonate sodium) (1:1) and poly(acrylamide‐co‐2‐acrylamido‐2‐methylpropanesulfonate sodium) (1:1) into an aqueous suspension of citrate‐stabilized AgNPs. The composites obtained were evaluated by an antibacterial activity assay on Staphylococcus aureus and Escherichia coli and subjected to an in vitro cytotoxicity assay for human fibroblasts. The composite formed from the hydrogel poly(N‐vinylpyrrolidone‐co‐2‐acrylamido‐2‐methylpropanesulfonate sodium) with 3 mol % N,N‐methylene bisacrylamide showed the highest antibacterial activity and the least cytotoxicity among the composites tested; this makes it an excellent alternative as a potential dressing for the treatment of deep and exudative wounds. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 39644.     

Production of alkenyl succinic anhydrides from low‐erucic and low‐linolenic rapeseed oil methyl esters

Fatty acid methyl esters from low‐erucic and low‐linolenic rapeseed oil were used to produce alkenyl succinic anhydrides. A second‐order Doehlert uniform network design was used to investigate the influence of the reaction temperature and the molar ratio between the maleic anhydride and the main unsaturated rapeseed oil methyl esters on the yield of alkenyl succinic anhydride from methyl oleate. Further subjects of investigation were the conversion of methyl oleate, the formation of side reaction products, the Gardner color of the product and its viscosity, and finally the content of maleic anhydride remaining in the medium after the reaction. Alkenyl succinic anhydride from methyl oleate was isolated by column chromatography and analyzed by IR, ¹H‐ and ¹³C‐NMR and MS. The optimal reaction conditions for obtaining the maximum yield of alkenyl succinic anhydride from methyl oleate in the experimental domain (80%) were 210‐220 °C and a maleic anhydride/rapeseed oil methyl ester molar ratio of 1.5. However, the products synthesized in these conditions showed a high degree of viscosity (0.45 kg m^?1 s^?1), a very dark color (18 Gardner color) and a high content of undesirable side products (6%), which could hinder their industrial use. A molar ratio of less than 1.5 led to a clearer and less viscous product, although with a lower alkenyl succinic anhydride content.