Epoxidized Soybean Oil Research Articles

Large amplitude oscillatory shear (LAOS) and Fourier transform rheology of ultrasonically extruded epoxidized soybean oil colloids containing organically modified nanoclay

LAOS studies were carried out on untreated and ultrasonically treated ESO/nanoclay 30B colloids obtained by means of an ultrasonic twin-screw extruder at 100 and 400 rpm and ultrasonic amplitudes of 5, 10 and 13 μm. Obtained results were used to perform Fourier transform. Waveform, 3D stress response, elastic and viscous Lissajous curves show significant differences between the untreated colloids and colloids treated at 10 and 13 μm. G1′ and G1″ of colloids are increased with increase of ultrasonic amplitude, as a result of better nanoclay dispersion at higher ultrasonic amplitudes. A higher screw rotation speed also improved nanoclay dispersion for untreated colloid and colloid treated at 5 μm. However, for colloid treated at 10 and 13 μm, a lower screw rotation speed resulted in a better dispersion. This is due to less asymmetric bubble collapse and more jet flow in ultrasonic zone at lower screw speed, which promotes dispersion. Colloids treated at 10 and 13 μm showed yielding and then a non-linearity at a higher strain amplitude compared with untreated colloids. The values of GM′ and ηL′ of colloids calculated from intracycle data exhibited the densification and filler network breakup much more observable than those seen on values of G1′ and G1″. This means GM′ and ηL′ are more suitable for description of colloids with a two-step yielding behavior. Parameters S and T calculated based on intracycle data showed enormous differences in the strain hardening/softening and shear thickening/thinning behaviors between the untreated colloid and the colloids treated at 10 and 13 μm.

The thermal and combustion properties of soybean oil phosphate-based polyurethane foam composites containing polyol of etidronic acid

In this work, a phosphorus-containing soybean oil-based polyol (PSOP) was successfully synthesized from epoxidized soybean oil by a ring-opening reaction with dibutyl phosphate. A phosphorous polyol (HEDP-PO) was synthesized by polymerization between 1-hydroxyethylidene-1,1-diphosphonic acid (HEDP) and propylene oxide (PO). The two new polyols were used together in the formation of flame-retardant polyurethane foams (FRPUF), which depicted good thermal stability and flame retardancy performance. The addition of PSOP/HEDP-PO polyols resulted in a reduction of cell size and an increasement of cell numbers of PUF composites, whose apparent density was observed to increase. Besides, the LOI value of PUF-80 could reach 23.7% and satisfy the V-0 rating in the vertical burning test. The cone calorimeter test showed a reduction in the heat release rate from 395 kW/m2 to 251 kW/m2 and the total heat release from 24.9 MJ/m2 to 18.0 MJ/m2. Polyurethane foam exhibited good flame retardancy because PSOP/HEDP-PO played a great free radical quenching effect in the gas phase by releasing the PO* and PO2* free radicals. Meanwhile, a more dense and complete carbon layer was formed to cut off the transfer of heat and oxygen between the matrix and the ambient.

Bio-Based Epoxy Resins of Epoxidized Soybean oil Cured with Salicylic acid Loaded with Chitosan: Evaluation of Physical–Chemical Properties

Bio-Based Epoxy Resins of Epoxidized Soybean oil Cured with Salicylic acid Loaded with Chitosan: Evaluation of Physical–Chemical Properties

Bio-based vitrimers from divanillic acid and epoxidized soybean oil

Bio-based vitrimers based on dynamic transesterification were cured from divanillic acids and epoxidized soybean oil. These materials exhibited satisfactory thermal and mechanical properties, and could be reprocessed at high temperatures.

Blowing tough polylactide film enabled by the in situ construction of covalent adaptive networks with epoxidized soybean oil as dynamic crosslinks

PLA covalent adaptive networks with ESO as dynamic crosslinks enhance the melt strength of PLA and enable the tough PLA film by extrusion blowing, opening up a new avenue toward advanced PLA film in response to severe plastic film pollution.

A solvent-free and scalable method to prepare alkali soluble soybean oil-based epoxy acrylic resin for photoresist application

The raw materials of commercial resin for photoresists nearly all come from petroleum resources. To follow the policy of “green chemistry”, it is urgent to employ renewable, biodegradable, green biomass resources instead of petroleum for the construction of photoresist resin. In this study, the alkaline soluble biobased epoxy acrylic resins are successfully prepared via a ring-opening reaction of epoxidized soybean oil (ESO) with the modified acrylic precursor (MMHEA), followed by diisocyanate modifying to introduce a small amount of polyurethane. The structures of the precursor and product resin are characterized and determined by FT-IR and 1 H NMR analysis. Subsequently, the properties of the resins and the related UV-curable coating films are tested detailedly. The results show that the product resin modified by diisocyanate possesses significantly improved viscosity (higher than 123 Pa s), and the UV-curable coating film containing hexamethylene diisocyanate has a moderate crosslinking density of 1443.18 mol m -3 and the excellent mechanical performances with the tensile strength of 20.40 ± 0.53 MPa, elongation at break of 30.74 ± 1.00% and toughness of 4.44 ± 0.11 MJ m -3 . Moreover, the UV-curable coating films can dissolve completely in 10 wt% NaOH solution at room temperature within 40 min. The prepared product resin is in line with the requirements of photoresist, which can be used in the printed circuit boards. This study develops and provides a solvent-free and one-pot method to prepare biobased epoxy acrylic resins, which are suitable to use as photoresist resin. The use of biomass raw materials and green UV-curing technology follows the principles of green chemistry. And the preparation method of biobased functionalized resins with universal applicability can be easily extended to use in large-scale industrial resin production construction. • A renewable polyfunctional resin was prepared from epoxy soybean oil. • The UV-curable resin with alkali solubility can be used for the photoresist. • Good toughness, thermal stability and crosslinking density properties of resin. • The utilization rate can reach 100% by solvent-free and one-pot method. • The resin can be used in large-scale industrial production applications.

Effects of biopolymer functionalization and nanohydroxyapatite heat treatment on the tensile and thermomechanical properties of Bone-Inspired 3D printable nanocomposite biomaterials

Bone-inspired biopolymer nanocomposite grafts are an alternative to conventional bone substitutes if designed to offer a structure with adequate mechanical properties and biocompatibility. In this study, a set of novel 3D printable bone-inspired nanocomposite biomaterials was developed to investigate the effects of additional cross-linking of the biopolymer matrix and heat treatment of nHA particles on the tensile and thermo-mechanical properties of these nanocomposites used in extrusion-based 3D printing. We observed that additional functionalization of acrylated epoxidized soybean oil (AESO), as the main component of the biopolymer matrix, with additional methacrylate groups (mAESO), increased the strength and elastic modulus of extruded nanocomposites by more than three times, as well as doubled the glass transition temperature due to an increased degree of crosslinking in the functionalized matrices. The mAESO-based nanocomposite filaments demonstrated a strength safety factor of 1.5 against the minimum required standard mechanical properties for bone cement according to ISO standard5833. While heat treatment of nHA reduced the frequency of larger agglomerations, no significant difference in mechanical properties was observed. These novel 3D printable nanocomposite biomaterials with their improved strength, modulus and thermo-mechanical properties could be suitable candidates for fabricating complex ‘by design’ 3D printed grafts and scaffolds for bone reconstruction.

Application of Epoxidized Soybean Oil in Highly Filled Water-Swelling Rubbers

Application of Epoxidized Soybean Oil in Highly Filled Water-Swelling Rubbers

Photocuring and digital light processing 3D printing of vitrimer composed of 2-hydroxy-2-phenoxypropyl acrylate and acrylated epoxidized soybean oil

Photocuring and digital light processing 3D printing of vitrimer composed of 2-hydroxy-2-phenoxypropyl acrylate and acrylated epoxidized soybean oil

Unveiling the reactivity of epoxides in carbonated epoxidized soybean oil and application in the stepwise synthesis of hybrid poly(hydroxyurethane) thermosets

In this work, the crosslinking reaction of partially carbonated epoxidized soybean oils with diamines was investigated through an unprecedented combination of in situ infrared and Raman spectroscopies, revealing two crosslinking regimes.

Cellulose-based films with internal plasticization with epoxidized soybean oil

A process was developed combining two natural-based products to obtain bio-based films. Industrial cellulose pulp was dissolved and mixed with epoxidized soybean oil (ESBO), which acts as an internal plasticizer. A distillable and recyclable ionic liquid-based solvent was used to dissolve the cellulose. Appropriate distribution of the cellulose/ESBO solution on glass surfaces and careful regeneration of the cellulose enabled the development of solvent-free and flexible cellulose films. Fourier transform infrared spectroscopy revealed the presence of the triglyceride structure and the absence of the epoxide ring in the films, confirming the chemical reaction between the hydroxyl and epoxide groups of cellulose. The resulting films were further characterized by scanning electron microscopy, dynamic scanning calorimetry, thermogravimetry, and mechanical tensile tests. The films were also evaluated by contact angle measurement, swelling ability, in vitro degradability and cytotoxicity. The results showed that the presence of ESBO can adjust both the flexibility and hydrophilicity of the cellulose films, resulting in materials suitable for a variety of applications.

Tannin-Epoxidized Soybean Oil as Bio-Based Resin for Fabrication of Grinding Wheel.

Formaldehyde-free epoxidized soybean oil-based resin has been prepared under acidic conditions by co-condensation of the epoxidized soybean oil and condensed tannin originating from agricultural and forestry sources as the main raw materials, whereas 1,6-hexanediamine was employed as a cross-linking agent. Fourier transform infrared spectroscopy (FTIR) and electrospray ionization (ESI) corroborated that tannin and epoxidized soybean oil underwent crosslinking under acidic conditions supported by hexamethylenediamine. A bio-based grinding wheel was fabricated by formulation of the developed resin with wood powder as source of grinding particles. The appearance, hardness, compressive strength and wear resistance of the resulting grinding wheel were studied. The results have shown that the grinding wheel possesses a smooth surface with no bubbles or cracks, and its hardness and wear resistance were greater than that of a phenolic resin-based grinding wheel. Interestingly, the grinding wheel incorporates more than 90% of its raw materials as biomass renewable materials; thus, it is generally considered non-toxic. In addition, the future feasibility of this approach to replace some petrochemical resins that are frequently used in the fabrication of grinding wheels is considered.

Fully bio-based hydroxy ester vitrimer synthesized by crosslinking epoxidized soybean oil with doubly esterified starch

Catalyst-free fully bio-based hydroxyester (BHE) vitrimers were synthesized by crosslinking and plasticizing epoxidized soybean oil with synthesized acetylated starch succinate monoesters to investigate the effects of different starch structures on the properties of the BHE vitrimers. The BHE vitrimers possessed a lower glass transition temperature as well as better solvent resistance and reprocessing performance compared to traditional starch-based materials. Owing to dynamically covalent bonds, the migration and exudation of plasticizers were avoided. A maximum strain of 230 % was achieved to prevent the retrogradation and brittleness of starch-based materials. Furthermore, the mechanical properties remained unchanged after three reprocessing cycles. Consequently, the obtained BHE vitrimers are eco-friendly and sustainable.

Functionalized Soybean Oil- and Vanillin-Based Dual Cure Photopolymerizable System for Light-Based 3D Structuring.

A novel dual cure photopolymerizable system was developed by combining two plant-derived acrylic monomers, acrylated epoxidized soybean oil and vanillin dimethacrylate, as well as the thiol monomer pentaerythritol tetrakis (3-mercaptopropionate). Carefully selected resin composition allowed the researchers to overcome earlier stability/premature polymerization problems and to obtain stable (up to six months at 4 °C) and selectively-polymerizable resin. The resin demonstrated rapid photocuring without an induction period and reached a rigidity of 317.66 MPa, which was more than 20 times higher than that of the other vanillin-based polymers. Improved mechanical properties and thermal stability of the resulting cross-linked photopolymer were obtained compared to similar homo- and copolymers: Young's modulus reached 4753 MPa, the compression modulus reached 1634 MPa, and the temperature of 10% weight loss was 373 °C. The developed photocurable system was successfully applied in stereolithography and characterized with femtosecond pulsed two-beam initiation threshold measurement for the first time. The polymerization threshold of the investigated polymer was determined to be controlled by the sample temperature, making the footprint of the workstations cheaper, faster, and more reliable.

ОСОБЛИВОСТІ ВПЛИВУ ЕПОКСИДОВАНОЇ СОЄВОЇ ОЛИВИ НА ВЛАСТИВОСТІ ПОЛІЛАКТИДНИХ МАТЕРІАЛІВ

Polylactide composite materials with the plasticizer-compatibilizer epoxidized soybean oil, which are filled with organic filler starch and inorganic – calcium carbonate, have been developed. Based on instrumental methods of analysis, the influence of epoxidized soybean oil on the features of physicochemical interactions in the system was investigated. A change in the rheological and thermophysical properties of the developed polylactide materials was established depending on the component composition.

Improving adhesion and antiaging properties of soybean oils-based pressure sensitive adhesives by phenolic acids grafting

Three representative natural phenolic acids (ferulic acid: 1 hydroxyl group, caffeic acid: 2 hydroxyl groups, and gallic acid : 3 hydroxyl groups) were selected to investigate the effects of phenolic acids grafting on adhesion and antiaging properties of soybean oils-based pressure sensitive adhesives (PSAs). The grafting of gallic acid and ferulic acid led soybean oils-based PSAs to occur cohesive failures due to their large sterohindrance, while the grafting of caffeic acid did not. The optimal conditions for caffeic acid-grafted soybean oils-based PSA preparation were 0.6% caffeic acid, 7% phosphoric acid, reaction temperature of 50 °C and reaction time of 6 min. Under the optimal conditions, caffeic acid-grafted soybean oils-based PSA had the shear adhesion of more than 99 h, 180˚ peel strength of 2.30 N/cm, and loop tack of 0.97 N, which are approximately 5 and 3 times the control (soybean oils-based PSA without caffeic acid grafting: 180˚ peel strength of 0.46 N/cm and loop tack of 0.35 N), respectively. The grafting of caffeic acid significantly slowed down the aging rate of soybean oils-based PSAs as the peel strength residue reduced from 871.29% to 157.06% (82% decrease). Characteristic results showed that caffeic acid-grafted soybean oils-based PSA had better optical transparency (light transmittance: >100% vs. >95%), higher thermal stability (rapid decomposition temperature: 365 vs. 350 °C; maximum decomposition temperature: > 850 vs. 481 °C) and lower glass transition temperature (−12.70 vs. −5.40 °C) than the control. • Phenolic acids were grafted onto epoxidized soybean oils for PSA preparation. • Gallic or ferulic acid grafting led soybean oils-based PSA to occur cohesive failure. • Caffeic acid grafting enhanced the 180˚ peel strength and loop tack by 5 and 3 times. • Caffeic acid grafting delayed PSA aging with peel strength residue reduced by 82%. • Resulting PSA had higher thermal stability and lower glass transition temperature.

Preparation of Bio-Based Foams with a Uniform Pore Structure by Nanocellulose/Nisin/Waterborne-Polyurethane-Stabilized Pickering Emulsion

Bio-based porous materials can reduce energy consumption and environmental impact, and they have a possible application as packaging materials. In this study, a bio-based porous foam was prepared by using a Pickering emulsion as a template. Nisin and waterborne polyurethane (WPU) were used for physical modification of 2,2,6,6-tetramethyl piperidine-1-oxyl-oxidized cellulose nanocrystals (TOCNC). The obtained composite particles were applied as stabilizers for acrylated epoxidized soybean oil (AESO) Pickering emulsion. The stability of the emulsion was characterized by determination of the rheological properties and microscopic morphology of the emulsion. The emulsion stabilized by composite particles showed better stability compared to case when TOCNC were used. The porous foam was obtained by heating a composite-particles-stabilized Pickering emulsion at 90 °C for 2 h. SEM (scanning electron microscopy) images showed that the prepared foam had uniformly distributed pores. In addition, the thermal conductivity of the foam was 0.33 W/m·k, which was a significant decrease compared to the 3.92 W/m·k of the TOCNC foam. The introduction of nisin and WPU can reduce the thermal conductivity of the foam, and the physically modified, TOCNC-stabilized Pickering emulsion provides an effective means to preparing bio-based porous materials.

Efficient utilization of peach gum to prepare UV-responsive peelable pressure-sensitive adhesives for non-destructive fabrication of ultrathin electronics

Restricted by the poor solubility and complex structure, it remains a significant challenge to efficiently convert raw peach gum (RPG), a natural plant gum comprised of polysaccharides, into usable polymer materials. Herein, a novel approach is reported to prepare UV-responsive peelable pressure-sensitive adhesives (PSAs), which are mainly applied in the manufacturing of ultrathin electronics, through efficient utilization of RPG via prior dissolution using the N,N-dimethylacetamide/lithium chloride (DMAc/LiCl) solvent system and later degradation using H2O2 under UV light at room temperature. With sorbitol-based polyurethane acrylate (SPUA) as a UV-curable oligomer, rosin as a tackifier, and epoxidized soybean oil (ESO) as a plasticizer, before UV irradiation, the 180° peel strength of the prepared PSAs reached 244.4 N/m. A short period of UV irradiation caused a formed cross-linked network structure inside the PSA and a disruption of the adhesive interface, resulting in a sharp decrease of 180° peel strength to 7.3 N/m to achieve a non-destructive peeling of the adherend electronics from the carrier. This work provides a feasible strategy for efficiently utilizing natural peach gum to prepare bio-based UV-responsive peelable PSAs.

Natural source compatibilizers for olive waste/recycled polypropylene matrix composites

AbstractA simple, environmentally friendly process was developed for surface hydrophobization of cellulose‐rich waste to improve their compatibility with recycled polypropylene (rPP), helping reduce costs while recycling environmentally problematic waste such as solid olive waste (also called olive pomace). In this study, an improvement of the interfacial bonding strength between the hydrophilic waste particles and the hydrophobic matrix was achieved by surface hydrophobization of the waste using a ring‐opening polymerization reaction of epoxidized soy‐bean oil (ESBO) with SnCl2 as a catalyst. The treatment on cellulose based filter paper led to a contact angle of 128°. The composite containing treated olive pomace has shown an increase in the elongation of 92% and an increase in the stress at yield of 15%, indicating improved compatibility.

Bio-based Polyurethane Derived from Carbon Dioxide and Epoxidized Soybean Oil

The synthesis of polyurethane relies on a toxic and petroleum-based isocyanate reactant. The aim of this research was to synthesize Polyurethane using environment-benign and renewable starting materials such as carbon dioxide and soybean oil. The carbonated soybean oil was first prepared from carbon dioxide (CO2) and epoxidized soybean oil (ESBO) using zinc glutarate (ZnGA) as a catalyst but the result of FTIR indicated the absence of the peak of cyclic carbonate around 1800 cm-1. Therefore, in this work, the synthesis of Polyurethane was modified from A. Lee (Lee & Deng, 2015) using tetramethylammonium bromide (TBAB) as a catalyst. The as-synthesized carbonated soybean oil (CSBO) was allowed to react with two types of substances, 3-aminopropyltriethoxysilane or diethylenetriamine with the molar ratios of cyclic carbonate:NH2 of 1:1 with THF or DMF as solvents to obtain Polyurethanes (U1THF, U1DMF, U2THF, U2DMF). After 3 hours lignin solution was added to form a film. Raman spectra confirmed the catalyst removal from CSBO. FTIR spectra showed the peak around 1800 cm-1 assigned to cyclic carbonate of CSBO, and a new peak of urethane linkage around 1700 cm-1 (C=O stretching) of Polyurethanes. The conversion of epoxide to cyclic carbonate was also confirmed by 1H-NMR. Upon adding lignin into the Polyurethanes, the lignin-urethane U1THF, and U1DMF formed films whereas U2THF, and U2DMF formed viscous liquids. In terms of applications, all four formulations can be potentially applied as bioadhesives.