Vegetable Oil Estolide Plasticizers for PVC

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Solution Overview

Problem

Current plasticizers, primarily petroleum-derived phthalates, have limitations in terms of environmental impact and versatility, prompting the need for alternative, vegetable oil-derived compounds that can effectively plasticize polymers like PVC while offering improved properties.

Innovation Solution

The development of estolide esters from vegetable oils with high unsaturation, specifically soybean, canola, and sunflower oils, which are modified to create estolide functionalities through a process involving oxidation and acylation reactions, enhancing their plasticizing capabilities when combined with polymers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If petroleum-derived phthalate plasticizers are used, then plasticizing efficiency is achieved, but environmental harm and health concerns increase

Engineering Contradiction:
Improveplasticizing efficiencyVSAvoidenvironmental harm
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters by using vegetable oil fatty acids with specific iodine values (120-180) and controlling the degree of esterification (70-100%) to create estolide esters that provide effective plasticizing while eliminating the harmful environmental and health effects of phthalates

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces expensive and harmful petroleum-derived phthalates with cost-effective vegetable oil-based estolide esters that can be produced from renewable resources, providing a sustainable alternative that is both economically viable and environmentally friendly

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Object-generated harmful factors

If vegetable oil-derived plasticizers are used, then environmental sustainability is improved, but plasticizing efficiency may be reduced

Engineering Contradiction:
Improveenvironmental sustainabilityVSAvoidplasticizing efficiency
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The invention optimizes key parameters including selecting vegetable oils with high iodine values (120-180) indicating high unsaturation, controlling esterification degree (70-100%), and adjusting molecular weight distribution to achieve plasticizing efficiency comparable to or exceeding traditional phthalates while maintaining environmental sustainability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures through estolide esterification where fatty acid chains are linked via ester bonds to form complex molecules with optimized properties, combining the benefits of renewable vegetable oils with enhanced plasticizing performance through controlled molecular architecture

Inventive Principle:
Principle #40Composite materials

3Reliability

If high iodine value vegetable oils are used to create estolide esters, then plasticizing efficiency is enhanced, but manufacturing complexity increases

Engineering Contradiction:
Improveplasticizing efficiencyVSAvoidmanufacturing complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention performs preliminary selection of vegetable oils with high iodine values (120-180) before the esterification process, ensuring that the starting materials have the necessary unsaturation level to form effective estolide esters, which simplifies the overall manufacturing process by avoiding the need for additional modification steps

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention controls the esterification reaction parameters including temperature, catalyst selection, and reaction time to achieve the desired degree of esterification (70-100%) while maintaining simplicity in the manufacturing process, balancing product performance with ease of production

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

These estolide esters demonstrate improved thermal stability and plasticizing efficiency, as evidenced by enhanced tensile properties and glass transition temperature changes in PVC formulations, compared to traditional plasticizers like DOP and Soft-n-Safe, indicating a more effective and sustainable alternative.

Implementation Method 1

treating the vegetable oil fatty acid alkyl esters with an oxidizing agent to form a reaction product comprising epoxy and hydroxyl groups covalently bonded to the fatty acid alkyl esters at the site of unsaturation

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

treating the reaction product with an acylating agent to react the epoxy and hydroxyl groups to form estolide esters covalently bonded to the unsaturated fatty acid alkyl esters

Methodology Applied
Scientific EffectAcylation: Chemical Bonding

Data Source

PatentUS9315650B2Bio-renewable plasticizers derived from vegetable oil
Publication Date: 2016.04.19 REGENTS OF THE UNIVERSITY OF MINNESOTA
  • US9315650B2 patent drawing
  • US9315650B2 patent drawing
  • US9315650B2 patent drawing

AI summary

A composition includes estolide esters of vegetable oil fatty acid alkyl esters where the vegetable oil has an unsaturation greater than 90 IV. The fatty acid alkyl esters include unsaturated and saturated fatty acid alkyl esters, and each unsaturated fatty acid alkyl ester has greater than one estolide ester functionality.