Alkenyl Succinic Anhydride Research Articles

Impact of hydrophobically modified cellulose nanofiber on the stability of Pickering emulsion containing insect protein.

Cellulose nanofiber (CNF) is an ideal Pickering emulsion stabilizer because of its high aspect ratio and flexibility. CNF was hydrophobically modified by dodecenyl succinic anhydride and used to stabilize the simulated food emulsion system containing insect protein. The prepared dodecenyl succinate nanofiber (D-CNFs) was characterized by contact angle and laser particle size analyzer. The stability of the emulsion system under different conditions was characterized by zeta potential and appearance observation. Lastly, in vitro digestion simulation experiments were carried out to investigate whether the addition of D-CNFs had an effect on the digestion and absorption of oil. The modification process for dodecenyl succinic anhydride to CNFs was that the system temperature was 40 °C, the system pH value was 8.5 and the reaction time was 6 h. The water contact angle of the modified CNFs increased to 83.2 ± 0.9°. D-CNFs were introduced into the simulated food emulsion system containing insect protein. The increase in the concentration of D-CNFs in the aqueous phase promoted the stability of the simulated emulsion system. Increasing the ratio of insect protein was not conducive to the stability of the emulsion. The final fat digestibility of the emulsion with D-CNFs was lower than that of the emulsion without D-CNFs. Overall, the analysis and characterization results show the potential of the modified CNF as a food simulant emulsion stabilizer containing insect protein, which can be used for the development of specific functional foods. © 2024 Society of Chemical Industry.

Structure and physicochemical properties of rice starch modified with dodecenyl succinic anhydride and its use for microencapsulating Pediococcus acidilactici probiotic

Polysaccharides are used as wall materials to extend the shelf life of lactic acid bacteria. Ice crystal formation during freezing leads to probiotic death. We prepared a series of dodecenyl succinic anhydride (DDSA)-modified rice starches with varying degrees of substitution and compared their functional properties. Fourier-transform infrared spectroscopy, X-ray diffraction analysis, and nuclear magnetic resonance results confirmed successful DDSA modification and the disruption of the long-range ordering of starch molecules. The structural changes modified the physicochemical properties of starch. For example, the apparent viscosity and viscoelastic characteristics of modified rice starch increased, and its freeze-thaw stability and emulsion capacity were remarkably improved after DDSA modification. Moreover, the modified starches exhibited promising performance for microencapsulating Pediococcus acidilactici. This study describes a rice starch derivative with excellent physicochemical properties that can be used to enhance the storage stability of bioactive probiotics.

Innovative bamboo-plastic composites interfacial compatibility design approach: Self-assembled crosslinked structure of polydopamine with acylated chitin fibers

Achieving interfacial compatibility through sustainable methods is a key objective in natural fiber-plastic composites research, aimed at optimizing mechanical performance. This study introduced an innovative organic bamboo-plastic composite (BPC) interfacial layer, incorporating O-acylated chitin fibers densely coated with polydopamine (PDA) via a mild and facile self-assembly method. Chitin nanofibers were acylated with dodecenylsuccinic anhydride in a deep eutectic solvent in a one-pot process. The resulting BPCs exhibited significantly enhanced mechanical properties, with tensile strength, flexural strength, modulus, and impact strength increased by 73.64 %, 39.19 %, 15.42 %, and 63.57 %, respectively, compared to untreated BPCs. This improvement highlights the effectiveness of tailoring cross-linked networks across heterogeneous interfaces in providing strength, dissipating strain, and promoting interfacial compatibility. Furthermore, these modified BPCs demonstrated enhanced thermal stability, crystallization behavior, and moderate hydrophobicity. This surface treatment strategy offers a distinctive approach to producing high-performance, eco-friendly BPCs, also facilitating the processing and utilization of marine biological resources on a wide scale.

Towards sustainable and recyclable plastic materials: Vanilin-based epoxy bio-composites with spruce bark powder and hydrochar, pioneering green chemistry solutions for shape memory applications

The negative impacts of fossil-based plastic production and its excessive usage are significant and multifaceted, affecting both the planet and humanity in various ways. In this study, a novel approach to developing sustainable and recyclable materials sourced from lignocellulosic biomass is introduced. This methodology involves formulating an epoxy-based resin using diglycidyl ether of vanillin (DGEVA) for curing with dodecenylsuccinic anhydride (DDSA), in presence of significant proportions (5–20 wt%) of either spruce bark (SB) powder or its hydrochar (HTC). Through thermomechanical analyses conducted via Dynamic Mechanical Analysis (DMA), it was ascertained that while the inclusion of SB has minimal impact on material performance, the incorporation of HTC leads to significant improvements. Specifically, a substantial enhancement in storage modulus is observed, increasing from 1.5 GPa to 3.1 GPa, and a rise in the damping factor from 56°C to 61°C. These findings are further corroborated by Scanning Electron Microscopy (SEM) analysis, which demonstrates excellent compatibility between the bioresin matrix and the biofillers. Moreover, this investigation underscores the remarkable mechanical and chemical recycling capabilities of the systems, which are notably improved by the presence of spruce bark or HTC particles, in addition to their inherent shape-memory properties. This approach not only showcases the feasibility of sustainable material development but also highlights the potential for an effective waste utilization in enhancing material properties and reducing the environmental impact.

Effects of synchronous intermissive multi-ultrasound and esterification dual modification on functionalities of starch and its emulsion stabilization ability

Dodecenylsuccinic anhydride (DDSA) has been widely used to obtain amphiphilic starches. In this study, we investigated the functionalities of synchronous intermissive multi-ultrasound-assisted esterified starch. Compared to native starch (NS), it was deduced that multi-ultrasound-modified starch (US), esterified starch (ES), and multi-ultrasound-assisted esterified starch (UES) exhibited increased viscosities but reduced gelatinization temperatures and thermal stabilities. The viscoelastic moduli, retrogradation behaviors and hydrophobicity of the ES and UES species significantly altered. Moreover, the results of structural characterization suggested that esterification reduced the molecular weight and structural order of starch, whereas the intermissive ultrasonication treatment did not aggravate the structural disruption of ES. Additionally, compared with NS and US, the emulsification abilities of the ES and UES specimens were improved, leading to the desirable effect of stabilizing astaxanthin. Overall, this study provides a method for preparing amphiphilic starch, which can be exploited as a potential emulsifier and emulsion stabilizer for bioactive compounds.

The potency of hydrophobic modification of alginate for a self-assembly matrix in fish oil encapsulation

To act as an emulsifier and a matrix for fish oil encapsulation, alginate is required to be modified due to its hydrophilicity. The purpose of this study was to modify alginate using dodecenyl succinic anhydride (DSA) under pH-controlled conditions and to apply it for stabilizing emulsion and encapsulating fish oil. The modification that followed the first-order reaction improved the hydrophobic properties of alginate as shown by the reduction of surface tension but improving the water contact angle, with CMC of 0.18 mg/l. A higher concentration of modified alginate was better in stabilizing fish-oil emulsion than the native one, as supported by the results of zeta potential, viscosity, and droplet size of the emulsion. Freeze-dried particle of this modified alginate emulsion showed better encapsulation efficiency and oxidation protection ability. Thermal properties of alginate were changed after hydrophobic modification and oil encapsulation. The freeze-dried particles of this modified alginate emulsion showed better encapsulation efficiency and protection ability. This study confirmed the protective ability of the modified alginate using DSA as an oil-based active ingredient encapsulant.

Effect of Temperatures on Modification of Alginate Hydrophobicity using Dodecenyl Succinic Anhydride

Alginate is a highly hydrophilic polysaccharide as it contains several hydroxyl groups in the main backbone chain. Some applications for example as surfactants, however, require alginate to have higher hydrophobic properties. Hence, attempts are conducted to improve its hydrophobicity. Dodecenyl succinic anhydride (DSA) has a long hydrophobic chain that could substitute the hydroxyl groups of alginate and improve its hydrophobic properties. This study aimed to produce modified alginates with higher hydrophobicity using DSA as a modifier. The alginate modification was conducted at 30-70oC. The result showed that the degree of substitution (DS) increased in short time and low temperature of reaction. The highest DS value (0.1515) was obtained at 30oC for 30 min which gave the highest viscosity (14.74 cps) and the lowest surface tension (94.08 mN/m). The viscosity and surface tension values for the native alginate were 9.53 cps and 162,98 mN/m, respectively. Meanwhile, the viscosity and surface tension of the lowest DS (0.083) were 11.06 cps and 119.63 mN/m, respectively. The attachment of the dodecenyl succinic group was confirmed by the IR spectra as the presence of ester groups in the modified alginate.

Effects of molecule weight on the emulsifying properties of dodecenyl succinic anhydride modified glucuronoxylans

Abstract Glucuronoxylans have been considered as an alternative polymer for petroleum polymers in coatings, films, emulsifiers, and other industries. In this study, different molecule weight glucuronoxylans were obtained through xylanase hydrolysis. Dodecenyl succinic anhydride (DDSA) was used as a modifying agent to functionalize glucuronoxylans. At the same degree of substitution (DS), higher molecule weight glucuronoxylans led to better emulsifying properties and emulsion stability. Higher molecule weight DDSA modified glucuronoxylans showed smaller droplets size, lower zeta potential, higher EA (emulsifying activity) and better emulsion stability. These results suggested that molecule weight has positive impact on the emulsifying properties of DDSA modified glucuronoxylans. Furthermore, DS had positive impact on the emulsifying properties of DDSA modified glucuronoxylans.

Novel cellulose nanocrystal/metal-organic framework composites: Transforming ASA-sized cellulose paper for innovative food packaging solutions

In this study, a novel cellulose nanocrystal/metal-organic framework composite (MC) was developed as a stabilizer for alkenyl succinic anhydride (ASA) Pickering emulsions, demonstrating remarkable sizing performance and antimicrobial properties for advanced food packaging applications. The MCs exhibited superior emulsion stabilization capabilities compared to pure metal-organic frameworks, with the optimum MC concentration identified as 1.0 wt% CNC. The hydrophobicity of the sizing paper was found to be enhanced with increasing CNC content. The MC-ASA sized paper demonstrated commendable storage stability, robust gas adsorption, and resistance to water vapor or water droplets. The MCs-ASA sized paper showed excellent food preservation efficacy, maintaining the freshness of strawberries for up to seven days, compared to ASA-sized paper without MCs. The antimicrobial assays targeting Escherichia coli and Staphylococcus aureus highlighted the intrinsic antimicrobial properties of the MCs, contributing to the extended freshness of the encased strawberries. The water vapor barrier efficacy and water retention capabilities of MCs-ASA sized paper were found to be superior to those of the paper without MCs, emphasizing the potential of the developed composite as an innovative and effective food packaging solution. This study offers valuable insights into the synthesis and implementation of CNC/MOF composite particles for versatile applications in food packaging, water-resistant materials, and environmental protection.

High-strength and recyclable hydroplastic films from hydrophobic cellulose nanofibers produced via deep eutectic solvents

To alleviate the dilemma of plastic recycling, the development of sustainable bioplastics that are compatible with the environment throughout the whole material life cycle has received widespread attention. We report a vacuum-assisted filtration method for preparation of high-strength bioplastic films made from hydrophobic cellulose nanofibers that were obtained by esterification of natural cellulose with dodecenylsuccinic anhydride in recyclable deep eutectic solvent (triethylmethylammonium chloride/imidazole). The tensile strengths of the resultant hydrophobic films were 150.8 MPa and 94.8 MPa under dry and humid conditions, respectively. Importantly, these films could be programmed into various shapes, such as “U” shaped bracket, helix, and ring via a hydrosetting method and the strong hydrogen bonding interactions between cellulose nanofibers contributed to shape fixation. Benefiting from their hydroplastic properties, various shapes of bioplastic films could be reversibly engineered by kirigami, origami, and embossing. Meanwhile, the disposal of waste films followed the recycling route to regain hydrophobic cellulose nanofibers. This work provided a facile approach for the preparation of high-strength and recyclable hydroplastic cellulose nanofiber films.

Encapsulation of alkenyl succinic anhydride oil droplets in emulsions: Preparation, characterization, stability properties and application in papermaking

This paper aimed to explore the influence of the guar and xanthan gum complex (GG/XG) on the physicochemical properties, microstructure, and sizing efficiency of alkenyl succinic anhydride (ASA) loaded emulsions. The centrifugal stability of the emulsions was measured using a Turbiscan equipment, the droplets morphology through an optical microscopy, the size of droplets and its distribution through a Mastersizer, and the sizing efficiency through the penetration method. Furthermore, Cryo-SEM and CLSM were used to elucidate the adsorption mechanism of polysaccharides at the ASA-water interface. When the concentration of GG/XG exceeded 0.35%, the ASA emulsions displayed excellent stability and low viscosity, and no water separation was observed even after high-speed centrifugation. By absorbing GG/XG at the oil-water interface, a dense interfacial film was formed, which blocked any interaction between the oil and water, thus hindering the hydrolysis of ASA. The sizing degree of the paper sized by ASA emulsion stored for 2 h was still higher than 88 s. By encapsulating ASA in emulsions that are stabilized exclusively by natural polysaccharides, the need for surfactants is eliminated, which in turn decreases the amount of foam present in the papermaking process, thus making it a more environmentally friendly production method.

Understanding alkenyl succinic anhydride (ASA) size reversion due to autooxidation

Alkenyl succinic anhydride (ASA) is a sizing agent. The wettability of paperboard decreases when ASA is applied. The efficacy of ASA in board can be reversed under certain conditions, making the paper more hydrophilic and of lesser quality/value. Although it is broadly known that ASA size reversion is due to autooxidation in the presence of oxygen in air, the environmental parameters that initiate or catalyze this reaction are not well understood. Six different experimental set ups were used to understand how temperature, daylight, fluorescent light, ultravio-let (UV) light, and darkness affect oxidation of ASA. Cobb values and pyrolysis gas chromatography-mass spectrom-etry (Py-GCMS) results show that size reversion is not a simple oxidation. The oxidation reaction was found to be significantly light dependent. Temperature variations were found to have moderate effect on the chemical stability.

Alkenyl Succinic Anhydride: The Question of Covalent Bonding and Chemistry Considerations for Better Sizing—Review

Alkenyl Succinic Anhydride (ASA) is a sizing agent used in papermaking to increase the water repellency of paper. Almost 60 years after the introduction of the chemical in papermaking, scientists still have differing views on how ASA interacts with cellulose. Several experiments were conducted to bring more clarity to the ASA sizing mechanism, especially on the contentious question of ASA-cellulose covalent bonding or the esterification reaction between ASA and cellulose during papermaking. Herein, research papers and patents, including experiments and results, from the 1960s to 2020 were reviewed. Our investigation revealed that the ester bond formation between ASA and cellulose is insignificant and is not a prerequisite for sizing effectiveness; the main ASA-related material found in sized paper is hydrolyzed ASA or both hydrolyzed ASA and ASA salt. In addition, ASA emulsion stability and ASA emulsion retention are important for sizing efficiency improvement.

Computationally driven design of low dielectric-loss epoxy resin for medium-frequency transformers

The design of low dielectric-loss epoxy resin (EP) systems plays an important role in the insulation optimization of medium-frequency transformers (MFTs). Due to the diversity of EP and curing agents, the traditional design method inspired by dielectric-loss measurements cannot complete low dielectric-loss EP systems design in plentiful candidate EP systems. In this study, molecular dynamics (MD) computation was introduced to drive the design of a low dielectric-loss EP system for MFTs. By analyzing the relationship between the dielectric loss and molecular motion of the EP systems, two MD results were selected as descriptors to indicate the dielectric loss of EP systems, including mean square displacement and α-transition temperature. Eventually, the low dielectric-loss EP system blending EP, methyl tetrahydrophthalic anhydride, and dodecenyl succinic anhydride was effectively designed according to the descriptors. The rationality of the computationally driven design was verified by broadband dielectric spectroscopy measurement and the finite element method. Compared with previous EP systems, MFT insulated with the designed EP system had not only a 40% lower dielectric loss (9.79 W) but a higher overload capacity. This study provides an effective method for the design of low dielectric-loss EP systems.

IR SPECTROSCOPY AS A METHOD
 FOR INVESTIGATION OF THE STRUCTURE OF SUCCINIMIDE TYPE ADDITIVES ACTIVITY

In a study by infrared spectroscopy, the synthesized succinimide additives, as well as raw and intermediate components: polyisobutylene, maleic anhydride, polyethylene polyamnes and alkenyl succinic anhydride, were studied. Based on the results obtained, the dependences of the dispersing ability and IR spectra of additives were revealed. Ways of further research on the topic are outlined.

Partial hydrophobic modification of alginate using dodecenyl succinic anhydride for fish oil encapsulation

Background. As a hydrophilic compound, alginate needs to be modified to perform both as an emulsifier and matrix for fish oil encapsulation. Dodecenyl succinic anhydride (DSA) was selected for the modification due to its mild reaction conditions and the fact that no side product is generated. The purposes of this research were to prepare partial hydrophobic groups of modified alginate, which were subsequently used for a fish oil encapsulant. Material and methods. The viscosity average molecular weight (Mv) of commercial alginate was adjusted using sonication. The degraded alginate was modified using DSA by mixing alginates in the desired ratio for 4 h at pH = 10. The fish oil emulsion was stabilized using the modified alginate and subsequently freeze-dried to obtain fish oil particles. The effect of the Mv of alginate and the alginate-DSA ratio was analyzed for emulsion stability. The performance of native and modified alginate in fish oil encapsulation were also compared. Results. Alginate modification using DSA was influenced by the Mv of alginate as described by degree of substitution. This modification reduced the fish oil oxidation degree up to 8%. The modified alginate using 400 kg/mol and a mol ratio of 1:4 emulsion prevented separation for up to 18 h. The dynamic second-order model was well fitted to represent the separation emulsion (R2 > 0.89). The fish oil encapsulation using the modified alginate showed higher loading capacity, and better anti-rehydration properties than the native one. The use of modified alginate also reduced the degree of oxidation <4% after 24 h. Conclusion. Modification using DSA improved the alginate capability to stabilize the emulsion and encapsulating fish oil.

Dodecenyl succinic‐β‐cyclodextrin with high degree of substitution: Synthesis, characterization and evaluation

Abstractβ‐cyclodextrin (β‐CD) has the characteristics of safety, non‐toxicity, and a wide range of sources. It can be used in improving surface activity. However, due to the limitation of molecular polarity and solubility, its surface activity and emulsification ability are weak. Therefore, it is necessary to improve adsorption capacity on phase interface by hydrophobic modification. In this article, dodecenyl succinic‐β‐cyclodextrin (DDS‐β‐CD) with different substitution degree was prepared by esterification of β‐CD with dodecenyl succinic anhydride (DDSA) as the esterifying agent. The product was characterized by FT‐IR, 1H NMR, SEM, and TGA, respectively. Results showed that DDS was successfully introduced into β‐CD. Both the degree of substitution (DS) and productivity (P) increased with the addition of DDSA and can reach 0.283 and 85.8%, respectively, when the molar ratio of DDSA to β‐CD was 3:1. The modified cyclodextrin showed lower surface tension and higher foaming ability. Compared with octenyl succinic‐β‐cyclodextrin (OS‐β‐CD), it was found that the length of hydrophobic segment had a significant effect on the surface tension. Due to its unique properties, it can be used as a good emulsifier for oil‐in‐water emulsions and a host material for lavender flavor.

Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence.

Vegetable oils are bio-based and sustainable starting materials that can be used to develop chemicals for industrial processes. In this study, the functionalization of three vegetable oils (grape, hemp, and linseed) with maleic anhydride was carried out either by conventional heating or microwave activation to obtain products that, after further reactions, can enhance the water dispersion of oils for industrial applications. To identify the most abundant derivatives formed, trans-3-octene, methyl oleate, and ethyl linoleate were reacted as reference systems. A detailed NMR study, supported by computational evidence, allowed for the identification of the species formed in the reaction of trans-3-octene with maleic anhydride. The signals in the 1H NMR spectra of the alkenyl succinic anhydride (ASA) moieties bound to the organic chains were clearly identified. The reactions achieved by conventional heating were carried out for 5 h at 200 °C, resulting in similar or lower amounts of ASA units/g of oil with respect to the reactions performed by microwave activation, which, however, induced a higher viscosity of the samples.

Xylan assisted construction of highly hydrophobic wood surface

Forming a nano-structured rough surface and incorporating synthetic low surface energy polymers is one of the major methods to construct a highly hydrophobic wood surface. However, most of the synthetic polymers are petroleum-based chemicals, which are toxic, non-biodegradable and lack the ability to well disperse the nanoparticles to construct an excellent nano-structured rough surface. In this study, xylans were modified by esterification reaction between dodecenyl succinic anhydride (DDSA) and the hydroxyls on xylans under alkaline condition. The DDSA modified xylans were used as a dispersant and an anchoring agent to uniformly disperse SiO2 nanoparticles and bind them on wood surface to construct a rough nano-structure. The DDSA modified xylans also demonstrated high hydrophobicity and low surface energy. The coating with SiO2 nanoparticle/DDSA modified xylan dispersions with an air-drying strategy has successfully led to a highly hydrophobic wood surface with a contact angle up to 131°. This study suggests the potential applications of xylans in the construction of highly hydrophobic wood surface for wood protection.

Recycled PLA – Wood flour based biocomposites: Effect of wood flour surface modification, PLA recycling, and maleation

• The recycling of PLA, after one-process, had substantial effect on the overall crystallinity. • The addition of wood, even in small inclusions (2.5 wt%), had substantially improved the PLA crystallinity. • Modification of wood fiber with DDSA had pronounced effects on the WPC’s water absorption properties. • Substitution of pristine wood to DDSA-modified wood has no effect on mechanical properties. • Synergistic effects of maleated-PLA and DDSA-modified wood further enhanced WPCs water-resistant properties. This study investigated the effects of simulated recycling of PLA and Maleated PLA using thermo-mechanical processes on its structure and physico-chemical properties and combined with pristine and modified wood flour (WF) for biocomposites. The WF modification entails a base catalyzed reaction of dodecenylsuccinic anhydride to effectively reduce its polarity and enhance the system’s compatibility. Recycling of PLA had a profound effect on PLA’s crystallinity and modulus. The addition of WF had significantly affected PLA’s crystallinity and moduli of the fabricated biocomposites. The modified samples had superior water repellent and dimensional stability capabilities of the wood-plastic composites.