Epoxy-Functionalized Fatty Acid Esters as Plasticizers

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Solution Overview

Problem

Petroleum-derived plasticizers used in thermoplastic polymers, such as PVC, are expensive, non-renewable, and pose health concerns due to endocrine disruption, necessitating a safer and more cost-effective alternative that is compatible with these materials.

Innovation Solution

Development of fatty acid esters functionalized with epoxy, acyloxy, and alkoxy groups derived from unsaturated fatty acid esters, which are prepared through partial epoxidation, ring-opening, acylation, and further epoxidation processes, offering a compatible and effective alternative as plasticizers and acid scavengers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If petroleum-derived plasticizers (e.g., DOP, DAP) are used to achieve flexibility and pliability in thermoplastic polymers, then the desired physical characteristics are obtained, but health concerns arise due to endocrine disruption and the materials are expensive and non-renewable

Engineering Contradiction:

Improveendocrine disruptionVSAvoidperformance as plasticizer

Core Design Contradiction:

Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent modifies the chemical structure of vegetable oil derivatives by introducing epoxy groups and acyloxy/alkoxy substitutions on adjacent carbon atoms. These parameter changes in molecular structure enable the derivatives to achieve compatibility with thermoplastic polymers while maintaining the safety advantages of renewable resources, thus resolving the contradiction between health safety and plasticizer performance

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining fatty acid ester moieties with epoxy groups and adjacent acyloxy/alkoxy groups. This composite approach integrates the safety and renewability of vegetable oils with the polymer compatibility characteristics needed for effective plasticization, eliminating endocrine disruption concerns while maintaining reliability

Inventive Principle:

Principle #40Composite materials

2Object-affected harmful factors

If unmodified vegetable oils are used as plasticizers to provide renewable and safe alternatives, then cost and safety are improved, but compatibility with thermoplastic polymers is poor

Engineering Contradiction:

ImprovetoxicityVSAvoidcompatibility with thermoplastic polymers

Core Design Contradiction:

Object-affected harmful factorsVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by chemically modifying vegetable oil derivatives through epoxidation and adjacent acyloxy/alkoxy substitution. These structural modifications transform unmodified vegetable oils into derivatives with enhanced polarity and intermolecular interaction capabilities, enabling them to compatibilize with thermoplastic polymers while preserving the low toxicity and renewable advantages

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention introduces local quality changes by placing specific functional groups (epoxy, acyloxy, and alkoxy) at particular positions within the fatty acid ester structure, specifically with acyloxy and alkoxy groups on adjacent carbon atoms. This localized functionalization creates regions of enhanced polarity and interaction capability that enable polymer compatibility without compromising the overall safety and renewability of the vegetable oil derivative

Inventive Principle:

Principle #3Local quality

3Adaptability or versatility

If modified derivatives of vegetable oils (e.g., epoxidized soybean oil) are used as plasticizers, then compatibility with thermoplastic polymers is improved, but further performance improvement is needed

Engineering Contradiction:

Improvecompatibility with thermoplastic polymersVSAvoidperformance as plasticizer

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The patent creates a composite molecular structure that combines epoxidized fatty acid ester moieties with adjacent acyloxy and alkoxy groups. This composite approach builds upon the compatibility improvements of epoxidized vegetable oils while adding further functional groups to enhance plasticizer performance, achieving both good compatibility and superior reliability

Inventive Principle:

Principle #40Composite materials

Solution Approach 2:

The invention merges multiple functional modifications (epoxidation, acylation, and alkylation) into a single integrated molecular structure with epoxy groups and adjacent acyloxy/alkoxy groups. This combination of modifications synergistically enhances both polymer compatibility and plasticizer performance, overcoming the limitations of single-modification approaches

Inventive Principle:

Principle #5Merging (Combining)

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

The resulting compounds provide improved performance and safety as plasticizers and acid scavengers, reducing the need for petroleum-derived materials while maintaining compatibility with thermoplastic polymers, and can be used in various applications including PVC formulations and personal care products.

Implementation Method 1

partial epoxidation, ring-opening, acylation, and further epoxidation processes

Methodology Applied

Scientific EffectEpoxidation: Oxidation

Data Source

PatentUS9586918B2Unsaturated fatty acid ester-based compositions useful as plastic additives

Publication Date: 2017.03.07 CARGILL INC

AI summary

Compositions useful as plastic additives may be prepared from renewable resources such as vegetable oils by functionalizing an unsaturated fatty acid ester with epoxy, acyloxy, and optionally alkoxy groups.