Isosorbide Epoxide Diesters as Bio-Based PVC Plasticizers

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Solution Overview

Problem

Current plasticizers used in PVC, such as phthalates, are environmental pollutants and pose health risks, necessitating the development of bio-based alternatives with equivalent plasticizing properties.

Innovation Solution

Epoxidized esters of isosorbide, specifically isosorbide oleic, linoleic, and linolenic acids, and their mixtures, which are highly compatible with PVC, characterized by their dry-blending time and ability to produce cohesive, flexible, and strong PVC plates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If phthalate-based plasticizers are used in PVC, then plasticizing properties and flexibility are improved, but environmental pollution and health risks increase

Engineering Contradiction:

Improveplasticizing abilityVSAvoidenvironmental pollution

Core Design Contradiction:

Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of plasticizers by using esters of 1,4:3,6-dianhydrohexitols (isosorbide, isomannide, isoidide) instead of traditional phthalates. These bio-based esters maintain the required plasticizing properties while eliminating the harmful environmental and health effects of phthalates, thus resolving the contradiction between plasticizing ability and environmental safety

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs readily available bio-based compounds (anhydrohexitols and their esters) that can be produced from renewable resources. These substitutes replace long-used but harmful phthalates with equally effective but environmentally benign alternatives, addressing both the functional requirement and the environmental concern

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Strength

If phthalate-based plasticizers are used in PVC, then flexibility and elongation at break are improved, but toxicity and health hazards increase

Engineering Contradiction:

Improveelongation at breakVSAvoidtoxicity

Core Design Contradiction:

StrengthVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by substituting toxic phthalates with non-toxic esters of 1,4:3,6-dianhydrohexitols. These bio-based esters provide equivalent or superior flexibility and elongation properties without the toxic effects, thereby resolving the contradiction between mechanical performance and safety

Inventive Principle:

Principle #35Parameter changes

3Ease of operation

If conventional plasticizers are used, then PVC flexibility is improved, but manufacturing time and processing complexity increase

Engineering Contradiction:

ImprovePVC flexibilityVSAvoidmanufacturing time

Core Design Contradiction:

Ease of operationVSProductivity

Solution Approach 1:

The patent uses esters of 1,4:3,6-dianhydrohexitols that are pre-designed to have optimal compatibility with PVC resin. This preliminary optimization of molecular structure ensures rapid absorption and homogeneous distribution during mixing, reducing manufacturing time while maintaining excellent flexibility without requiring complex processing steps

Inventive Principle:

Principle #10Preliminary action

4Ease of operation

If non-bio-based plasticizers are used, then plasticizing performance is achieved, but environmental sustainability deteriorates

Engineering Contradiction:

Improveplasticizing performanceVSAvoidenvironmental sustainability

Core Design Contradiction:

Ease of operationVSReliability

Solution Approach 1:

The patent fundamentally changes the origin parameter of plasticizers from petrochemical-based phthalates to bio-based esters of 1,4:3,6-dianhydrohexitols. These naturally derived esters maintain all required plasticizing functions while being environmentally sustainable and biodegradable, thus resolving the contradiction between performance and sustainability

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 epoxidized esters demonstrate superior compatibility and plasticizing ability, enhancing PVC flexibility and transparency while reducing environmental impact and manufacturing time.

Implementation Method 1

the mechanism of action of which relies on a reduction of the intermolecular forces in the PVC resin, thereby enabling the macromolecules of vinyl chloride to 'slide' more freely over one another

Methodology Applied

Scientific EffectPlasticization:

Implementation Method 2

By increasing the 'free volume' between the polymer chains, they lower the glass transition temperature of the PVC, which contributes to making the latter more flexible

Methodology Applied

Scientific EffectGlass transition temperature reduction:

Data Source

PatentUS10113053B2Isosorbide epoxide diesters, and the use thereof as a plasticizer in PVC compositions

Publication Date: 2018.10.30 ROQUETTE FRERES SA

AI summary

The invention relates to isosorbide epoxide esters having Formulas (I), (II), and (III), to the mixtures thereof, and to the use thereof as an additive in PVC compositions, particularly as a plasticizer.