Bio-based Diols from HMF for Sustainable Coatings

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Solution Overview

Problem

Current diols used in polymer synthesis are predominantly derived from petroleum, and there is limited attention given to diols with a furan skeleton derived from cellulosic biomass.

Innovation Solution

Development of novel diols derived from 5-hydroxymethyl furfural (HMF), diformyl furan (DFF), or their derivatives, along with the synthesis of diglycidyl ethers from these diols, which can be used in composites, adhesives, and curable coating compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If petroleum-based diols are used for polymer synthesis, then current industrial production standards are met, but sustainability and depletion of fossil fuels become problematic

Engineering Contradiction:
ImprovesustainabilityVSAvoidfossil fuel depletion
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The invention changes the source material parameter from petroleum-based to bio-based feedstocks (HMF, DFF, FDCA). This substitution maintains the functional properties needed for polymer synthesis while improving sustainability and reducing dependence on depleting fossil fuel resources

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses readily available, inexpensive bio-based feedstocks (HMF, DFF, FDCA) that can be produced from renewable biomass sources. These short-living, renewable materials replace long-lived fossil fuel resources, providing a sustainable alternative that aligns with circular economy principles

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

2Reliability

If diols with furan skeleton from cellulosic biomass are used, then sustainability is improved, but limited attention and lack of established methods exist

Engineering Contradiction:
ImprovesustainabilityVSAvoidmanufacturing methodology
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The invention performs preliminary actions by establishing complete synthesis pathways from bio-based feedstocks (HMF, DFF, FDCA) to diol monomers and their glycidyl ether derivatives. These pre-developed methodologies provide ready-to-use routes for manufacturing sustainable polymer materials, eliminating the need for separate method development

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention segments the synthesis process into distinct, manageable steps: (1) obtaining diols from HMF/DFF/FDCA through specific chemical transformations, (2) synthesizing glycidyl ether derivatives from these diols, and (3) applying them in polymer synthesis. This segmentation makes the complex bio-based manufacturing process easier to implement and scale

Inventive Principle:
Principle #1Segmentation

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 use of these novel diols and diglycidyl ethers offers a sustainable alternative for polymer synthesis, leveraging bio-based feedstocks and potentially improving the properties of polymers and coatings.

Implementation Method 1

The diols are prepared by the reaction of a Grignard reagent with 5-hydroxymethyl furfural or diformyl furan

Methodology Applied
Scientific EffectGrignard reaction: Chemical Bonding

Implementation Method 2

The diglycidyl ethers are prepared from the diols and epichlorohydrin

Methodology Applied
Scientific EffectEpoxy formation reaction: Chemical Bonding

Data Source

PatentEP3997077B1Novel bio-based diols from sustainable raw materials, uses thereof to make diglycidyl ethers, and their coatings
Publication Date: 2025.05.21 NORTH DAKOTA STATE UNIV RES FOUND
  • EP3997077B1 patent drawing
  • EP3997077B1 patent drawing
  • EP3997077B1 patent drawing

AI summary

The invention relates to diols derived from 5-hydroxymethyl furfural, diformyl furan, or derivatives thereof. The invention further relates to diglycidyl ethers derived from the diols of the invention, curable coating compositions containing the diglycidyl ethers, and objects coated with the curable coating compositions. The invention also relates to composites, composites, adhesives, and films containing the diglycidyl ethers of the invention. The invention also relates to methods of making the diols, diglycidyl ethers, and curable coating compositions.