Levulinic Derivative Adducts for Non-Toxic PVC Plasticizers

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Current plasticizers for polymers, particularly PVC, are often derived from non-renewable petroleum sources, are expensive, toxic, and have harmful environmental impacts, with some compounds acting as endocrine disruptors.

Innovation Solution

Development of ester compounds from renewable materials like unsaturated fatty acid esters and levulinic acid esters, which are reacted to form ketals, providing a compatible and non-toxic plasticizer for various industrial polymers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If petroleum-derived plasticizers are used, then plasticizing performance is achieved, but environmental harm and toxicity increase

Engineering Contradiction:

Improveplasticizing performanceVSAvoidenvironmental harm and toxicity

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters by using levulinic acid esters and epoxidized fatty acid esters as raw materials to synthesize new plasticizer compounds with molecular structures that provide effective plasticizing performance while eliminating the toxicological and environmental harm associated with conventional petroleum-derived plasticizers

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention employs renewable, inexpensive raw materials (levulinic acid esters and epoxidized fatty acid esters) to create plasticizers that are environmentally benign and can be readily produced, replacing expensive and harmful petroleum-derived alternatives with sustainable, short-lived renewable resources

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Adaptability or versatility

If epoxidized triglycerides are used as plasticizers, then renewable material usage is achieved, but compatibility with PVC is limited

Engineering Contradiction:

Improverenewable material usageVSAvoidcompatibility with PVC

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The invention modifies the molecular structure parameters by reacting levulinic acid esters with epoxidized fatty acid esters to create adducts with specific functional groups and molecular weights that enhance compatibility with PVC while maintaining the renewable character of the original materials

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining levulinic acid ester components with epoxidized fatty acid ester components, producing adducts that integrate the beneficial properties of both materials to achieve both renewability and PVC compatibility

Inventive Principle:

Principle #40Composite materials

3Reliability

If dicarboxylic acid esters are used, then excellent plasticizing properties are achieved, but synthesis complexity and cost increase

Engineering Contradiction:

Improveplasticizing propertiesVSAvoidsynthesis complexity and cost

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The invention changes the synthesis pathway parameters by using readily available levulinic acid esters and epoxidized fatty acid esters as starting materials with simple reaction conditions (mixing and heating), avoiding the complex multi-step synthesis required for dicarboxylic acid esters while achieving comparable plasticizing properties

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention employs inexpensive, easily obtainable raw materials (levulinic acid esters and epoxidized fatty acid esters) that can be produced from renewable resources, replacing expensive dicarboxylic acid esters that require complex synthesis, thereby reducing both material cost and manufacturing complexity

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

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 ester compounds offer excellent compatibility and plasticizing properties across a range of polymers, including PVC, poly(3-hydroxyalkanoates), and polysaccharides, while being environmentally benign and cost-effective.

Implementation Method 1

Epoxide groups of monoepoxidized unsaturated fatty acid esters are reacted with levulinic esters in the presence of a suitable catalyst, typically a protic acid or a Lewis acid, to form ketals of levulinic esters of dihydroxylated fatty acid esters

Methodology Applied

Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS8686169B2Adducts of levulinic derivatives with epoxidized fatty acid esters and uses thereof

Publication Date: 2014.04.01 GFBIOCHEM

AI summary

The present disclosure relates to methods of preparation of compounds resulting from the reaction of levulinic esters and epoxidized unsaturated fatty acid esters. The compounds are useful as renewable biomass-based plasticizers for a variety of polymers. Mono-, di- and tri-ketal adducts formed in a reaction between alkyl esters of levulinate and epoxidized unsaturated fatty acid esters derived from vegetable oils are also disclosed.