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Pressure-Sensitive Adhesives Based on Epoxidized Soybean Oil and Dicarboxylic Acids

Pressure-Sensitive Adhesives Based on Epoxidized Soybean Oil and Dicarboxylic Acids
Learning Objets
Summary
This learning object examines the development of environmentally friendly pressure-sensitive adhesives (PSAs) synthesized from epoxidized soybean oil (ESO) and bio-based dicarboxylic acids via an epoxide–acid reaction. The study investigates the influence of crosslinking density, monomer ratios, and curing conditions on adhesive performance, including tack, peel strength, and shear resistance. The resulting PSAs demonstrate competitive adhesive properties compared to petrochemical-based counterparts while utilizing renewable resources. Through systematic variation of composition and processing, the research illustrates how bio-based polymers can be tailored for targeted applications in adhesives, reducing environmental impact without sacrificing functionality.

This work embodies the principles of green chemistry by replacing petroleum-derived PSA components with renewable, plant-based feedstocks, specifically soybean oil and dicarboxylic acids. It demonstrates:
1. Use of renewable feedstocks by employing ESO and bio-based acids.
2. Designing safer chemicals by reducing the use of volatile organic compounds common in PSA formulations.
3. Energy efficiency via mild reaction conditions and solvent-free synthesis.
4. Design for degradation by using biodegradable monomers that support end-of-life environmental compatibility.

Students can learn how chemical structure influences material properties, how renewable feedstocks can meet industrial performance standards, and how to integrate sustainability principles into polymer and adhesive design.

Authors: Mengmeng Li, Hongbo Li, Jinwen Zhang, Fang Xu, Shuaishuai Ma, and Haihong Wu.
Citation: Li, M., Li, H., Zhang, J., Xu, F., Ma, S., & Wu, H. (2014). Pressure-sensitive adhesives based on epoxidized soybean oil and dicarboxylic acids. Industrial Crops and Products, 52, 221–228. https://doi.org/10.1016/j.indcrop.2013.10.032.
Learning Goals/Student Objectives
By the end of studying this article, students should be able to:

1. Understand the motivation for developing biobased pressure-sensitive adhesives (PSAs)
--Explain the environmental and sustainability concerns associated with petroleum-based PSAs.

2. Describe the advantages of using plant oils like epoxidized soybean oil (ESO) in polymer synthesis.
--Describe the chemical principles behind PSA formulation
--Identify the role of epoxidized soybean oil and dicarboxylic acids in forming hydroxyl-functionalized polyesters.
--Explain the ring-opening reaction between epoxy and carboxylic acid groups and its significance in cross-linking.

3. Analyze the impact of different dicarboxylic acids on PSA properties
--Compare the effects of dimer acid (DA), sebacic acid (SA), adipic acid (AA), and difunctional polymeric carboxylic acid (DPCA) on peel strength, tack, and shear strength.
--Understand how molecular weight and structure of acids influence cross-linking density and adhesive performance.

4. Evaluate the role of catalysts in polymerization
--Discuss the effectiveness of AMC-2 and other catalysts in accelerating the epoxy-carboxylic acid reaction.

5. Interpret experimental data and characterization techniques
--Analyze FTIR and NMR spectra to monitor polymerization and curing.
--Understand ASTM testing methods for peel strength, loop tack, and shear strength.

6. Assess the environmental and practical implications of the research
--Evaluate the aging resistance and performance of the biobased PSAs.
--Discuss the potential for commercial application and environmental benefits of solvent-free, renewable PSA production.
Object Type
Journal articles
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Blended learning
Collaborative/cooperative learning
Green Chemistry Principles
Designing Safer Chemicals
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Use of Renewable Feedstocks
Design for Degradation
Real-Time Pollution Prevention
U.N. Sustainable Development Goals (SDGs)
Good Health and Well-Being
Industry, Innovation and Infrastructure
Climate Action
Life Below Water
Life on Land
Safety Precautions, Hazards, and Risk Assessment
Hazards and Risk Assessment
Chemical Hazards:
Epoxidized Soybean Oil (ESO): Generally considered low toxicity, but may cause skin or eye irritation. Handle with gloves and safety goggles.
Dicarboxylic Acids (DA, SA, AA): Can be irritants to skin, eyes, and respiratory tract. Use in a well-ventilated area and wear appropriate PPE.
Bisphenol A Diglycidyl Ether (BPAGE): Potential skin sensitizer and may cause allergic reactions. Handle with care and avoid inhalation or skin contact.
AMC-2 Catalyst (Chromium(III) 2-ethylhexanoate): Contains chromium compounds, which may be toxic or carcinogenic in certain forms. Use gloves, goggles, and work in a fume hood.
Solvents (used in solubility tests): Ethyl acetate, chloroform, THF, toluene, acetone, ether, DMF, and hexane are flammable and toxic. Use in a fume hood with proper PPE.

Thermal Hazards
Hot Melt Coating and Curing: Involves heating materials to 85–160 °C. Risk of burns from hot surfaces and molten materials. Use heat-resistant gloves and ensure proper thermal insulation.

Mechanical Hazards
Laminator and Coating Equipment: Risk of pinch points and mechanical injury. Operate with caution and follow manufacturer safety guidelines.

Safety Precautions
Personal Protective Equipment (PPE):
Lab coat, safety goggles, nitrile gloves
Heat-resistant gloves during thermal curing

Ventilation:
Conduct all reactions involving volatile chemicals or catalysts in a fume hood

Waste Disposal:
Dispose of chromium-containing waste and organic solvents according to institutional hazardous waste protocols

Emergency Preparedness:
Have access to eyewash stations and safety showers
Know the location of fire extinguishers and spill kits
NGSS Standards, if applicable
HS-ETS1: Engineering Design
HS-ETS1-3: Evaluate a solution to a complex real-world problem based on prioritized criteria and trade-offs.
The authors evaluate different formulations of PSAs based on peel strength, tack, shear strength, and environmental impact.

HS-ETS1-2: Design a solution to a complex real-world problem by breaking it down into smaller, more manageable problems.
The research breaks down PSA development into material selection, reaction optimization, and performance testing.

HS-ESS3: Earth and Human Activity
HS-ESS3-4: Evaluate or refine a technological solution that reduces impacts of human activities on natural systems.
The paper promotes renewable, plant-based materials (soybean oil) over petrochemical-derived adhesives, aligning with sustainability goals.

Crosscutting Concepts
Structure and Function: Understanding how molecular structure (e.g., epoxy groups, phenylene rings) affects adhesive properties.
Cause and Effect: How changes in chemical composition and curing conditions affect PSA performance.
Energy and Matter: Tracking energy input (heat) and matter transformation during polymerization.

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