Epoxidized linseed oil

• CAS: 8016-11-3
• Catalog Number: ACM8016113-1
• Category: Main Products
• Molecular Weight: 0
• Synonyms: ELO
• Flash Point: 310 °C
• Density: 1.034g/mL at 20°C(lit.)
• Physical State: Liquid

Case Study

Studies on the curing of epoxidized linseed oil

Ding, Cheng, et al. Green Chemistry 17.7 (2015): 4000-4008.

A cyclic dibasic acid has an effect on the thermal and mechanical properties of epoxy thermosets derived from epoxidized linseed oil (ELO). Different techniques were used, including differential scanning calorimetry (DSC), solvent extraction, FT-IR, NMR, dynamic mechanical analysis (DMA), tensile testing and thermogravimetric analysis (TGA). The results show that the obtained epoxy resins are highly crosslinked polymers with only small amounts of low molecular weight soluble materials. The glass transition temperature (T), tensile strength, Young's modulus, elongation at break and toughness decrease with increasing DCA chain length, while thermal stability increases.
13C NMR measurements of epoxidized linseed oil show that epoxy groups are present in the 54-58 ppm delta region. The 13C NMR peak present at 173.1 ppm is due to the carbonyl carbon of the triacylglycerols, and the peaks at 68.9 ppm and 62.1 ppm are assigned to the octyl carbon of -CH-CH-CH- and the methylene carbon of the -CH-CH-CH- backbone, respectively. Likewise, the extracted soluble material shows no characteristic epoxy peaks in the delta 54-58 ppm region in contrast to the epoxidized linseed oil. Solid-state 13C-NMR of the insoluble material clearly indicates the presence of a carbonyl/ester group at 174 ppm.

Characterization of epoxidized linseed oil

López Téllez, Enrique Vigueras-Santiago, and Susana Hernández-López. Superficies y vacío 22.1 (2009): 05-10.

Epoxidized linseed oil was prepared for varying different reaction parameters such as temperature, amount of peroxide and enzyme of the well-studied chemoenzymatic epoxidation method. The subsequent epoxidation reaction was followed by infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (HNMR), which are the most commonly used spectrometers for this proposal. However, micro-Raman spectroscopy and differential scanning calorimetry (DSC) characterizations were used as complementary techniques in this work.
A layer of liquid and oily samples (linseed oil (LO) and epoxidized linseed oil (ELO)) was distributed on the surface of a KBr disk. NMR spectra were recorded on the magnetic resonance for samples solved in CDCl3. The samples were introduced into the capillary and the measurements were performed directly on the top of the capillary. The heating rate from 30°C to 600°C was 20 °C/min under a nitrogen atmosphere (100 mL/min) and a platinum disk was used for the temperature increase. The pore size heat of reaction in joules per gram (J/g) was obtained by integrating the area under the curve of the corresponding exothermic transition in the DSC curve.

Effect of different curing agents on the curing of epoxidized linseed oil

Todorovic, Andrea, et al. Journal of Applied Polymer Science 138.16 (2021): 50239.

The effects of curing agent type and amount on the curing reaction and the resulting thermal and mechanical properties of epoxidized linseed oil were investigated in detail. Analysis of the curing mechanism showed that the optimal mixing ratio of bio-based epoxy resin and curing agent must be determined experimentally due to steric hindrance, side reactions and/or rapid gelation. The overall mechanical properties of the resulting resin range from soft and flexible to hard and rigid, depending on the type of curing agent applied, and can be used to form epoxy composites and coatings.
Epoxidized linseed oil was heated to 80 °C, then the catalyst was added and the mixture was stirred with a magnetic stirrer. After complete melting, the mixture was cooled to 40 °C and the curing agent was added. The mixture was further stirred for 5 min with a magnetic stirrer to homogenize. The amount of curing agent was systematically varied in order to evaluate the optimal resin formulation.

Preparation of bioresins using epoxidized linseed oil

Pin, Jean-Mathieu, Nicolas Sbirrazzuoli, and Alice Mija. ChemSusChem 8.7 (2015): 1232-1243.

Biorenewable resources can be used as green monomers to design tailored structures for formulations and can play an important role as functional materials. Preparation of biobased materials with toughened mechanical properties based on epoxidized linseed oil. The results were obtained by a holistic approach to the crosslinking process. Therefore, anionic alternating copolymerization of epoxides with mono- and dianhydrides was studied to tailor the parameters leading to maximum conversion and properties. The highly crosslinked networks obtained performed well, as evidenced by good impact strength, high glass transition temperature and excellent thermal stability, which opens the possibility of using these emerging materials for industrial applications.
The formulations were achieved by considering R = 1:0.8 and 1:0.5, so that the epoxy resin was in excess according to reports in the literature. The lack of anhydrides was required, considering the inability to complete the copolymerization due to steric hindrance and increased viscosity. Finally, the ratio of epoxidized linseed oil/MHHPA was selected to be 1:0.8 and the ratio of epoxidized linseed oil/BTDA to be 1:0.5. These epoxy/dianhydride ratios were determined based on the processability of the mixture and also to avoid early gelation during polymerization. To obtain a homogeneous mixture, the cured samples were prepared by adding the curing agent to the previously melted ELO. Finely divided initiator was then introduced at room temperature at 0.9% by weight.