Muconic Acid Unsaturated Polyesters via Vinyl Modification

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Solution Overview

Problem

Current methods for utilizing muconic acid in polymer production lack efficient processing and incorporation, limiting its economic and environmental benefits as a renewable platform molecule.

Innovation Solution

Development of a polymer and resin system that incorporates muconic acid through reactions with bioderived diols and dicarboxylic acids, followed by crosslinking with vinyl-terminated hydrocarbons, to create unsaturated polymers and composites with tunable thermal and mechanical properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If muconic acid is directly incorporated into polymers without further chemical processing, then economic and environmental benefits are improved, but processing efficiency and incorporation efficiency deteriorate

Engineering Contradiction:

Improveeconomic and environmental benefitsVSAvoidprocessing efficiency and incorporation efficiency

Core Design Contradiction:

Ease of manufactureVSProductivity

Solution Approach 1:

The patent applies preliminary action by pre-modifying muconic acid with vinyl groups before polymerization. This preliminary chemical modification enables the acid to participate efficiently in free radical polymerization processes, resolving the contradiction between direct use benefits and processing efficiency. The vinyl-modified muconic acid is prepared in advance and then incorporated into the polymer system.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical parameters of muconic acid by introducing vinyl functional groups, transforming it from a non-polymerizable acid to a polymerizable monomer. This parameter change enables efficient incorporation into vinyl-based polymers while maintaining the renewable feedstock advantage, thus resolving the contradiction between direct use and processing efficiency.

Inventive Principle:

Principle #35Parameter changes

2Stability of the object's composition

If muconic acid is used as a renewable feedstock, then sustainability is improved, but thermal stability and mechanical properties of the polymer deteriorate

Engineering Contradiction:

ImprovesustainabilityVSAvoidthermal stability and mechanical properties

Core Design Contradiction:

Stability of the object's compositionVSStrength

Solution Approach 1:

The patent creates composite materials by incorporating vinyl-modified muconic acid into existing polymer matrices alongside other monomers. This composite approach allows the renewable muconic acid component to provide sustainability benefits while the overall composite system maintains or enhances thermal stability and mechanical properties through the synergistic combination of multiple components.

Inventive Principle:

Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by strategically positioning vinyl-modified muconic acid units within the polymer chain at controlled concentrations. This localized incorporation ensures that the renewable feedstock provides sustainability benefits without compromising the overall structural integrity and performance of the polymer, as the muconic acid units are distributed optimally within the matrix.

Inventive Principle:

Principle #3Local quality

3Productivity

If vinyl-modified muconic acid is incorporated into free radical polymerization, then incorporation efficiency is improved, but polymerization control and molecular weight distribution deteriorate

Engineering Contradiction:

Improveincorporation efficiencyVSAvoidpolymerization control and molecular weight distribution

Core Design Contradiction:

ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies partial action by incorporating vinyl-modified muconic acid at controlled, moderate levels within the polymerization system rather than attempting complete substitution. This partial incorporation maintains good polymerization control and narrow molecular weight distribution while still achieving efficient incorporation of the renewable feedstock at optimal concentrations.

Inventive Principle:

Principle #16Partial or excessive action

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 approach enables the production of biobased unsaturated polymers and resins with improved thermal stability and mechanical properties, demonstrating the potential for muconic acid as a sustainable replacement in polymer applications.

Implementation Method 1

Development of a polymer and resin system that incorporates muconic acid through reactions with bioderived diols and dicarboxylic acids

Methodology Applied

Scientific EffectCondensation polymerization: Chemical Bonding

Implementation Method 2

followed by crosslinking with vinyl-terminated hydrocarbons, to create unsaturated polymers and composites

Methodology Applied

Scientific EffectCrosslinking: Chemical Bonding

Implementation Method 3

incorporation of the unsaturated polyester into a free radical polymerization system

Methodology Applied

Scientific EffectFree radical polymerization: Photopolymerisation

Data Source

PatentUS10280255B2Renewable resins and unsaturated polyesters and methods of making the same

Publication Date: 2019.05.07 ALLIANCE FOR ENERGY INNOVATION LLC

AI summary

An aspect of the present disclosure is a bioderived polymer that includes a first repeat unit that includeswhere n is an integer between 1 and 1000, and R1 is a first hydrocarbon group.