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Exploration of the complementary properties of biobased epoxies derived from rosin diacid and dimer fatty acid for balanced performance

Exploration of the complementary properties of biobased epoxies derived from rosin diacid and dimer fatty acid for balanced performance
Learning Objets
Summary
This learning object explores the synthesis, characterization, and performance evaluation of biobased epoxies derived from rosin diacid and dimer fatty acid, focusing on their complementary mechanical, thermal, and curing properties. The study presents a modified two-step synthesis of diglycidyl ester-type epoxies using calcium oxide as a water scavenger to improve yield and epoxy content. The rigid rosin-derived epoxy (diglycidyl ester of acrylopimaric acid) and the flexible dimer acid-derived epoxy (diglycidyl ester of dimer acid) were cured with nadic methyl anhydride, both individually and in blends, to investigate property balance. Analysis included DSC, DMA, flexural testing, and TGA. Results show that blending the rigid and flexible biobased epoxies in appropriate ratios (20–40 wt% dimer acid epoxy) achieves well-balanced toughness, stiffness, and thermal stability, illustrating their potential as renewable alternatives to petroleum-based bisphenol A epoxies.

Relation to Green Chemistry Learning
This work aligns with the principles of green chemistry by utilizing renewable feedstocks (rosin from pine trees and fatty acids from plant oils) to develop high-performance polymer materials. It addresses key sustainability goals:

Use of renewable resources: Employing rosin and plant-oil-derived dimer acids reduces reliance on fossil fuels.

Design for energy efficiency: The modified synthesis process improves yield and reduces waste generation.

Safer chemical synthesis: Avoidance of bisphenol A–based epoxies mitigates concerns over toxicity and environmental persistence.

Design for degradation: The use of biobased monomers enhances potential environmental compatibility at end-of-life.

This learning object can be used in a Green Chemistry curriculum to demonstrate how sustainable materials can meet or exceed the performance of petrochemical counterparts, reinforcing concepts of renewable feedstocks, functional property tailoring through molecular design, and life-cycle considerations.

Kun Huang, Jinwen Zhang, Mei Li, Jianling Xia, Yonghong Zhou. Exploration of the complementary properties of biobased epoxies derived from rosin diacid and dimer fatty acid for balanced performance. Industrial Crops and Products, volume 49, 2013, 497-506.
https://doi.org/10.1016/j.indcrop.2013.05.024.
Keyword Tags
Soy Chemistry
Biomaterials
Renewable Feedstocks
Organic Synthesis
Polymers
Biopolymers
Mechanical Properties
Link to external
Link to journal article
Learning Goals/Student Objectives
By engaging with this learning object, students will be able to:
1. Explain how renewable feedstocks such as rosin and plant-oil-derived dimer acids can be converted into high-performance epoxy resins.
2. Describe the relationship between molecular structure (rigid vs. flexible segments) and the resulting mechanical, thermal, and curing properties of polymers.
3. Analyze experimental data (DSC, DMA, TGA, flexural testing) to evaluate the performance of biobased epoxy systems.
4. Compare the advantages and trade-offs between biobased and petroleum-based epoxies in terms of sustainability, performance, and green chemistry principles.
5. Apply Green Chemistry concepts to the design and optimization of sustainable polymeric materials.
6. Evaluate how blending materials with complementary properties can lead to balanced performance in engineered systems.
Object Type
Case studies
Journal articles
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Blended learning
Green Chemistry Principles
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Use of Renewable Feedstocks
U.N. Sustainable Development Goals (SDGs)
Industry, Innovation and Infrastructure
Responsible Consumption and Production
Climate Action
Safety Precautions, Hazards, and Risk Assessment
Working with epichlorohydrin, sodium hydroxide, calcium oxide, acrylic acid, and curing agents such as nadic methyl anhydride requires strict adherence to chemical safety protocols. Epichlorohydrin is toxic, volatile, and a suspected carcinogen; it should be handled only in a well-ventilated fume hood while wearing appropriate PPE (lab coat, nitrile gloves, safety goggles, and, if necessary, a respirator). Sodium hydroxide and calcium oxide are strongly caustic and can cause severe skin and eye burns; use chemical-resistant gloves and avoid generating dust. Acrylic acid is corrosive and a strong irritant, with flammable vapors—keep away from ignition sources and handle under ventilation. Nadic methyl anhydride is a skin and respiratory sensitizer; avoid inhalation and skin contact, and work in a fume hood.

When heating reactions to high temperatures (≥230 °C), ensure proper thermal controls, shielding, and monitoring to prevent runaway reactions or splashes. Epoxy resins and curing agents can cause allergic skin reactions; avoid direct contact and promptly clean spills. Waste epichlorohydrin and other hazardous organics should be collected in labeled containers for disposal as hazardous waste, never poured down the drain.

A thorough risk assessment should identify the main hazards: chemical toxicity, skin/eye corrosion, flammability, high-temperature operations, and sensitization potential. Mitigation strategies include engineering controls (fume hood, splash guards), administrative controls (training, SOPs), and PPE. Emergency equipment—eyewash stations, safety showers, and spill kits—must be readily accessible, and all personnel should be trained in first-aid response to chemical exposure.
NGSS Standards, if applicable
High School – Physical Science (HS-PS)
HS-PS1-2 – Construct and revise an explanation for the outcome of a simple chemical reaction based on the outermost electron states of atoms, trends in the periodic table, and knowledge of chemical properties.
Applicable: Students can explain how rosin diacid and dimer fatty acid structures influence epoxy reactivity and curing behavior.
HS-PS2-6 – Communicate scientific and technical information about why the molecular-level structure is important in the functioning of designed materials.
Applicable: The study connects molecular rigidity/flexibility to performance properties like toughness, modulus, and Tg.

High School – Engineering, Technology, and Applications of Science (HS-ETS)
HS-ETS1-2 – Design a solution to a complex real-world problem by breaking it down into smaller, more manageable problems.
Applicable: Designing a sustainable epoxy system required addressing yield, curing, mechanical performance, and thermal stability.
HS-ETS1-3 – Evaluate a solution to a complex real-world problem based on prioritized criteria and trade-offs.
Applicable: The balance between renewable content, mechanical performance, and thermal stability demonstrates trade-off analysis.

High School – Earth and Human Activity (HS-ESS)
HS-ESS3-4 – Evaluate or refine a technological solution that reduces impacts of human activities on natural systems.
Applicable: Replacing petroleum-based bisphenol A epoxies with biobased alternatives supports sustainable material development.

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Submitted by

Kris Weigal
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Published
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Soy Chemistry Literature