Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol

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Solution Overview

Problem

Conventional polyurethane resins derived from petroleum-based succinic acid suffer from inconsistent physical properties, poor handling characteristics, and instability in polyurethane reactions due to impurities like malic acid, which are difficult to control and remove, limiting their practical application and environmental sustainability.

Innovation Solution

Control the content of malic acid, an organic acid with a pKa value of 25°C of not more than 3.7, during the production of polyester polyols from biomass resources to achieve a biopolyurethane with improved mechanical properties, flexibility, and reduced coloration, using a method that involves reacting aliphatic diols with dicarboxylic acids derived from biomass, ensuring a specified range of malic acid content in the dicarboxylic acid.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If polyester polyols are synthesized from adipic acid using nitric acid oxidation method, then production efficiency is improved, but environmental harm increases due to N2O emissions

Engineering Contradiction:
Improveproduction efficiencyVSAvoidN2O emissions
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter by replacing adipic acid with succinic acid as the dicarboxylic acid component. This substitution fundamentally alters the oxidation process, eliminating N2O emissions while maintaining production efficiency, as succinic acid can be produced via fermentation or other environmentally benign methods

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the environmental harm of N2O emissions into a benefit by using succinic acid-based polyester polyols that not only eliminate greenhouse gas emissions but also improve polyurethane reaction stability and physical properties, including coloration resistance and mechanical performance

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Ease of manufacture

If polyester polyols are produced from petroleum-derived succinic acid, then production cost is reduced, but product quality deteriorates due to malic acid impurities causing inconsistent physical properties

Engineering Contradiction:
Improveproduction costVSAvoidphysical property consistency
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent extracts and removes malic acid impurities from the succinic acid-based polyester polyol through purification processes. This extraction of harmful impurities maintains the cost-effectiveness of succinic acid while achieving consistent physical properties and stable polyurethane reaction characteristics

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the purity parameter of succinic acid by implementing controlled purification steps that reduce malic acid content to acceptable levels. This parameter optimization ensures both cost-effectiveness and manufacturing precision in the final polyurethane products

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If polyether type polyols are used, then flexibility and elasticity are improved, but mechanical strength deteriorates due to poor abrasion resistance and heat resistance

Engineering Contradiction:
ImproveflexibilityVSAvoidabrasion resistance
Core Design Contradiction:
Ease of operationVSStrength

Solution Approach 1:

The patent creates a composite polyol system by combining succinic acid-based polyester polyol with specific diols and chain extenders. This composite approach achieves a balance between flexibility and mechanical strength, overcoming the limitations of both polyether and conventional polyester polyols alone

Inventive Principle:
Principle #40Composite materials

4Temperature

If conventional polyester polyols are used, then heat resistance is improved, but hydrolysis resistance deteriorates due to ester group instability

Engineering Contradiction:
Improveheat resistanceVSAvoidhydrolysis resistance
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent changes the chemical structure parameter by using succinic acid with controlled purity and specific molecular weight distribution. This parameter optimization reduces the number of ester groups and improves chain stability, simultaneously enhancing both heat resistance and hydrolysis resistance in the resulting polyurethane

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

The approach results in a biopolyurethane with enhanced mechanical properties, improved flexibility, and reduced coloration, offering better handling and operational properties compared to petroleum-based polyurethanes, while being environmentally friendly and suitable for various applications such as synthetic leathers and adhesives.

Implementation Method 1

reacting an aliphatic diol and a dicarboxylic acid to produce a polyester polyol

Methodology Applied
Scientific EffectCondensation polymerization:

Implementation Method 2

reacting an aliphatic diol and a dicarboxylic acid to produce a polyester polyol

Methodology Applied
Scientific EffectEsterification:

Implementation Method 3

reacting the polyester polyol and a polyisocyanate compound

Methodology Applied
Scientific EffectPolyaddition:

Implementation Method 4

reacting the polyester polyol and a polyisocyanate compound

Methodology Applied
Scientific EffectUrethane formation:

Data Source

PatentEP3486267B1Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol
Publication Date: 2020.12.16 MITSUBISHI CHEM CORP
  • EP3486267B1 patent drawing
  • EP3486267B1 patent drawing
  • EP3486267B1 patent drawing

AI summary

The present invention relates to a biomass-resource-derived polyester polyol, which at least comprises, as constituent units, a dicarboxylic acid unit, an aliphatic diol unit, and an organic acid unit having a pKa value at 25°C of not more than 3.7, wherein the dicarboxylic acid contains at least one component derived from biomass resources, and a content of the organic acid unit is more than 0 % by mole and not more than 0.09 % by mole relative to the dicarboxylic acid unit; wherein the hydroxyl number-calculated molecular weight of the polyester polyol is 500 or more and not more than 4,000, the hydroxyl number-calculated molecular weight being calculated in the following manner while considering the polyol as a diol: Hydroxyl number−calculated molecular weight=Molecular weight of KOHg/mole/Hydroxyl numbermg−KOH/g×1,000×2.