Dioctyl Maleate Research Articles

Synthesis of a novel cationic hydrophobic shale inhibitor with preferable wellbore stability

To solve the problems of wellbore instability and collapse caused by clay hydration during the horizontal drilling process of shale gas, a novel cationic hydrophobic shale inhibitor ADD was synthesized by emulsion polymerization using acrylamide (AM), dioctyl maleate (DOM), dimethyl diallyl ammonium chloride (DMDAAC), and KH570-SiO2. Fourier transform infrared spectroscopy (FTIR) and Thermo Gravimetric Analysis (TGA) were used to characterize the functional groups and thermostability of synthesized material. The inhibition performance of shale inhibitor ADD was evaluated by the rolling recovery rate, linear expansion rate, and core immersion test. After being treated with 1% ADD for 16 h, the linear expansion rate of the core sample was 18%, the debris rolling recovery rate was 96.3%. The inhibition performance was better than that of polyamine inhibitor YZ and KCl. The Zeta potentials and contact angles measurement of core samples before and after treatment were measured, it was found that the Zeta potentials of core samples decreased significantly with the increasing concentrations of ADD. The possible explanation could be that ADD molecules with the positive charge can neutralize with the negative charge on the clay surface, reducing the repulsion force of the double electric layer of the clay. And the ADD molecules can form a hydrophobic adsorption layer with high roughness and low surface energy on the rock surface, which can reverse the wettability of shale from liquid-wetting to strong hydrophobicity, then preventing the intrusion of drilling fluid and formation water, achieving the inhibition of the hydration and expansion of shale.

Dual Catalytic Activity of Amberlyst-15 in the Large-scale and Sustainable Synthesis of Dioctyl Sodium Sulfosuccinate (DOSS)

Dioctyl sodium sulfosuccinate (DOSS) as a unique material both as a drug and surfactant was synthesized by a facile and economical synthetic method. In this project, Amberlyst-15 was selected as a heterogeneous recyclable bronsted solid acid for this synthesis both in the esterification of maleic anhydride and sulfonation of dioctyl maleate (DOM) ester. This catalyst was easily recovered and reused at least for 13 consecutive cycles without a significant loss in the catalytic activity. In this paper, we wish to uncover a catalytic approach for the synthesis of DOSS through a recyclable, easily recoverable, and commercially available catalyst, namely Amberlyst 15, under mild conditions.

Dioctyl maleate market to reach $326.1 M by 2026

Dioctyl maleate market to reach $326.1 M by 2026

The effects of feeding ratio on final properties of vinyl acetate-based latexes via semi-continuous emulsion copolymerization

Semi-continuous emulsion polymerization of vinyl acetate and dioctyl maleate (VAc/DOM) (60/40, w/w) was carried out with pre-emulsion feeding using potassium persulfate as an initiator. The influence of emulsifier type and its initial ratio were studied and the mixture of non-ionic emulsifiers; 30 and 10 mol ethoxylated nonylphenol (NP30 and NP10) at a ratio of 50/50 (w/w) provided better pre-emulsion and polymerization stability, and also final latex stability. In addition, two series of experiments were conducted to determine the effect of initiator and reactive surfactant, oligomeric N-methylol acrylamide (o-NMA) amount in the initial reactor charge on the latex properties. By increasing the initial initiator amount from 10 to 50 wt%, the average particle size of the latexes decreased from 203 to 143 nm. As expected, the amount of initiator strongly affected the particle charge and the highest zeta potential value was obtained when 50 wt% of the initiator was initially present in the reactor, showing the increased latex stability. On the other hand, it was detected that the colloidal properties of the copolymer latexes were significantly affected by the change of initial charge of o-NMA. The o-NMA amount exceeding 50 wt% caused coagulation. When all o-NMA was initially fed, the highest viscosity value, 9878 cP; lowest zeta potential value, − 5 mV; and the highest surface tension value, 37.5 mN m−1, were obtained. Consequently, the change in the initial charge of emulsifier, initiator, and reactive surfactant has played an important role on the colloidal stability of VAc/DOM latexes.

The effect of maleic acid diesters type on the stability of vinyl acetate emulsion polymers

Abstract Vinyl acetate (VAc) was copolymerized with two different maleic acid diesters, dibutyl maleate (DBM) and dioctyl maleate (DOM) at different comonomer ratios by semi-continuous emulsion polymerization method. The effects of maleic acid diesters type and amount on the latex properties of VAc emulsion polymers were investigated. The particle size, viscosity, zeta potential, surface tension and conductivity of the latexes were determined by Dynamic Light Scattering (DLS), Brookfield viscometer, zeta potential analyzer, Du Nouy tensiometer and electrical conductometer, respectively. The latex freeze-thaw stability and ionic strength resistance were also analyzed. The experimental results have shown that the variety in comonomer type and amount created significant differences on the latex properties of VAc emulsion polymers. With the use of DBM or DOM in a certain amount, the particle size and particle size distribution of VAc emulsion polymers were decreased while their latex stability were increased. DBM was also more effective in improving the latex stability than DOM. Consequently, it was clearly observed that these two comonomers enhanced the overall latex properties of VAc homopolymer depending on their type and amount.

Toxicogenomic Screening of Replacements for Di(2-Ethylhexyl) Phthalate (DEHP) Using the Immortalized TM4 Sertoli Cell Line.

Phthalate plasticizers such as di(2-ethylhexyl) phthalate (DEHP) are being phased out of many consumer products because of their endocrine disrupting properties and their ubiquitous presence in the environment. The concerns raised from the use of phthalates have prompted consumers, government, and industry to find alternative plasticizers that are safe, biodegradable, and have the versatility for multiple commercial applications. We examined the toxicogenomic profile of mono(2-ethylhexyl) phthalate (MEHP, the active metabolite of DEHP), the commercial plasticizer diisononyl cyclohexane-1,2-dicarboxylate (DINCH), and three recently proposed plasticizers: 1,4-butanediol dibenzoate (BDB), dioctyl succinate (DOS), and dioctyl maleate (DOM), using the immortalized TM4 Sertoli cell line. Results of gene expression studies revealed that DOS and BDB clustered with control samples while MEHP, DINCH and DOM were distributed far away from the control-DOS-BDB cluster, as determined by principle component analysis. While no significant changes in gene expression were found after treatment with BDB and DOS, treatment with MEHP, DINCH and DOM resulted in many differentially expressed genes. MEHP upregulated genes downstream of PPAR and targeted pathways of cholesterol biosynthesis without modulating the expression of PPAR’s themselves. DOM upregulated genes involved in glutathione stress response, DNA repair, and cholesterol biosynthesis. Treatment with DINCH resulted in altered expression of a large number of genes involved in major signal transduction pathways including ERK/MAPK and Rho signalling. These data suggest DOS and BDB may be safer alternatives to DEHP/MEHP than DOM or the commercial alternative DINCH.

Influence of Dioctyl Maleate Concentration on Performance Behavior of Water Based Pressure-sensitive Adhesives via Reversible Addition–Fragmentation Chain Transfer Emulsion Polymerization

Reversible addition–fragmentation chain transfer (RAFT)-mediated polymerization was successfully applied for the synthesis of pressure-sensitive adhesives (PSAs) of predetermined molar mass and of low polydispersity index (PDI). The performances of the adhesives were investigated by testing tack, peel, and shear resistance on seven different substrates (coated paper, uncoated paper, polyethylene terephthalate (PET), biaxially oriented polyethylene terephthalate (BOPP), aluminum strip, low linear density polyethylene (LLDPE), and low density polyethylene (LDPE). The influence of monomer composition on the adhesive performance was evaluated by varying the molar ratio of butyl acrylate (BA)/dioctyl maleate (DOM) while keeping the molar ratio of acrylic acid (AA) and 2-hydroxy ethyl acrylate (2-HEA) constant. As the DOM content increased, shear, peel strength, and loop tack were found to increase. It was noted that the adhesive properties of PSAs can be tailored by incorporating small amounts of hydrophobic DOM into the PSAs, which significantly increases the peel and shear strength of the resulting PSAs. Carboxyl terminated bifunctional trithiocarbonate RAFT agent possess the strong potential to polymerize hydrophobic DOM in aqueous phase and exhibit better living character with PDI less than 1.5.

Designing greener plasticizers: Effects of alkyl chain length and branching on the biodegradation of maleate based plasticizers

The ubiquitous presence of the plasticizer di (2-ethylhexyl) phthalate (DEHP) in the environment is of concern due to negative biological effects associated with it and its metabolites. In particular, the metabolite mono (2-ethylhexyl) phthalate (MEHP) is a potential endocrine disruptor. Earlier work had identified the diester di (2-ethylhexyl) maleate (DEHM) as a potential greener candidate plasticizer to replace DEHP, yet its biodegradation rate was reported to be slow. In this study, we modified the side chains of maleate diesters to be linear (i.e., unbranched) alkyl chains that varied in length from ethyl to n-octyl. The plasticization efficiency of these compounds blended into PVC at 29wt.% increased with the overall length of the molecule, but all compounds performed as well as or better than comparable samples with DEHP. Tests conducted with the equally long DEHM and dihexyl maleate (DHM) showed that branching has no effect on glass transition temperature (Tg) reduction efficiency. Biodegradation experiments with the common soil bacterium Rhodococcus rhodocrous in the presence of the plasticizer showed acceptable hydrolysis rates of maleates with unbranched side chains, while the branched DEHM showed almost no degradation. The addition of hexadecane as auxiliary carbon source improved hydrolysis rates. Temporary buildup of the respective monoester of the compounds were observed, but only in the case of the longest molecule, dioctyl maleate (DOM), did this buildup lead to growth inhibition of the bacteria. Maleates with linear side chains, if designed and tested properly, show promise as potential candidate plasticizers as replacements for DEHP.

Improvement of film properties of vinyl acetate based emulsion polymers by using different types of maleic acid diesters

Two types of maleic acid diesters, dibutyl maleate (DBM) and dioctyl maleate (DOM) were used as comonomers in semicontinuous emulsion copolymerization of vinyl acetate (VAc) in order to improve the film properties of poly(vinyl acetate), PVAc emulsion polymer. The effects of the comonomer type and comonomer ratio on minimum film forming temperature (MFFT), glass transition temperature (Tg), polymer structure, molecular weights, water contact angle and water resistance of PVAc latex films were examined. It was found that MFFT and Tg of the PVAc emulsion polymer decreased by the presence of the maleic acid disters in copolymer composition. This decrease was more affected by the increasing content and alkyl chain length of the comonomers. The molecular weights of the emulsion polymers were also affected by the comonomers and their ratios. Moreover, hydrophobicity and water resistance of the PVAc latex films were increased by using DBM and DOM as comonomer.

Lubricants Additives from Maleate Copolymers

This work aims to prepare and characterize dialkyl maleate via esterification of maleic anhydride with different alcohols (butanol, octanol, decyl alcohol, and dodecyl alcohol) to produce dibutyl maleate M1, dioctyl maleate M2, didecyl maleate M3, and didodecyl maleate M4. Then polymerization of the prepared dialkyl maleate with two different monomers (vinyl acetate and styrene) to produce dialkyl maleate-vinyl acetate copolymers (M1v, M2v, M3v, and M4v) and dialkyl maleate-styrene copolymers(M1S, M2S, M3S, and M4S). The molecular weight of the prepared copolymers were determined by using Gel Permeation chromatography (GPC) water 600E. The efficiency of the prepared copolymers for improving the viscosity index of the base lube oil was studied. It was found that the efficiency increases with increasing alkyl chain length of alcohol group in the prepared dialkyl maleat and increases with increasing the molecular weight of the prepared copolymers, and the efficiency of the prepared copolymers as viscosity index improvers for the lube oil increases with increasing the concentration of this compound in solution (base oil). It was also found that VI increases in presence of styrene monomer than that of vinyl acetate monomer.

Allergic contact dermatitis from dioctyl maleate in a moisturizer

Contact DermatitisVolume 55, Issue 4 p. 250-250 Allergic contact dermatitis from dioctyl maleate in a moisturizer Correction(s) for this article Corrigendum Volume 56Issue 1Contact Dermatitis pages: 60-60 First Published online: December 14, 2006 I. Chan, Corresponding Author I. Chan Department of Dermatology, St Mary’s Hospital, London W2 1NY, UKIen ChanDepartment of DermatologySt Mary’s HospitalPraed StreetLondon W2 1NYUKTel: +44 (0)20 7886 7992Fax: +44 (0)20 7886 1134e-mail: ien.chan@kcl.ac.ukSearch for more papers by this authorS. H. Wakelin, S. H. Wakelin Department of Dermatology, St Mary’s Hospital, London W2 1NY, UKSearch for more papers by this author I. Chan, Corresponding Author I. Chan Department of Dermatology, St Mary’s Hospital, London W2 1NY, UKIen ChanDepartment of DermatologySt Mary’s HospitalPraed StreetLondon W2 1NYUKTel: +44 (0)20 7886 7992Fax: +44 (0)20 7886 1134e-mail: ien.chan@kcl.ac.ukSearch for more papers by this authorS. H. Wakelin, S. H. Wakelin Department of Dermatology, St Mary’s Hospital, London W2 1NY, UKSearch for more papers by this author First published: 05 September 2006 https://doi.org/10.1111/j.1600-0536.2006.00909.xCitations: 6Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume55, Issue4October 2006Pages 250-250 RelatedInformation

Mechanical and thermal properties of poly(lactic acid)/starch blends with dioctyl maleate

AbstractPoly(lactic acid) (PLA)/starch blends were prepared blending with dioctyl maleate (DOM). DOM acted as a compatibilizer at low concentrations (below 5%), and markedly improved tensile strength of the blend. However, DOM functioned as a plasticizer at concentrations over 5%, significantly enhancing elongation. Compatibilization and plasticization took place simultaneously according to the analysis of, for example, mechanical properties and thermal behavior. With DOM as a polymeric plasticizer, thermal loss in the blends was not significant. Water absorption of PLA/starch blends increased with DOM concentration. DOM leaching in an aqueous environment was inhibited. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 94: 1697–1704, 2004

Formation of carbon spherules by pressure carbonization—Relation to molecular structure of precursor

Dioctyl and dicetyl esters and their mixtures with either polyethylene (PE) or polyvinylchloride (PVC) were carbonized at 650°C under a pressure of 30 MPa. Dioctyl phthalate, malonate, and succinate gave carbon spherules after pressure carbonization. The mixtures of dicetyl phthalate and succinate with PVC as well as those of dioctyl maleate and polyethylene terephthalate (PET) with PE also yielded carbon spherules. The esters are presumed to decompose thermally to the functional and hydrocarbon components, the former corresponding to the decomposition product of PVC and the latter to that of PE mixtures of which have been found to form carbon spherules by pressure carbonization. The ratio of the numbers of carbon atoms in these two components, R( f h ) , is required to be in the range of 0.8:16 to 1.8:16 in order to yield carbon spherules. The mixing ratio of the two organic precursors yielding carbon spherules can be estimated from the ratio R( f h ) , and can be adjusted to this range by adding either functional or hydrocarbon components.

Thermal degradation of poly(vinyl chloride) in alkyl maleates

AbstractThe thermal degradation of poly(vinyl chloride) has been investigated in diethyl, dibutyl and dioctyl maleate under nitrogen from 160°C to 210°C. The rate of dehydrochlorination was highest in dibutyl maleate and lowest in dioctyl maleate. The apparent activation energy calculated from the average value of the rate constant at each temperature for diethyl, dibutyl and dioctyl maleate was found to be 83.6 kJ mole−1, 112.7 kJ mole−1, and 150.5 kJ mole−1, respectively. The rates of dehydrochlorination and the activation energy observed in alkyl maleates are higher than those observed in ethyl benzoate. In the visible range spectra the absorption at higher wavelengths is considerably reduced in alkyl maleates.

Experimental study of copolymerization. II

AbstractIn order to study further the effect of structure on monomer reactivities in copolymerization the copolymer composition as a function of initial monomer mixture composition has been determined for the following monomer pairs: vinyl acetate–vinyl chloride, ethyl methacrylate–vinylidene chloride, butyl methacrylate–vinylidene chloride, vinyl acetate–tetrachloroethylene, allyl chloride–vinylidene chloride, vinyl acetate–vinylidenechloride, methyl methacrylate–vinyl chloride, pentene‐1–vinyl chloride, allyl chloride–vinyl acetate, methyl methacrylate–2,5‐di‐chlorostyrene, vinyl chloride–vinylidene chloride, and vinyl chloride–dioctyl maleate.