Hydroxyacetal Monomers for Polyurethane Degradation

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Solution Overview

Problem

Current methods for disposing of polyurethanes are inefficient and environmentally harmful, as they require high energy incineration and lack sustainable degradation solutions.

Innovation Solution

Development of hydroxyacetal or hydroxyketal monomers that can be incorporated into polyurethane products, enabling acid-catalyzed degradation at room temperature and producing new hydroxy-functional polymer intermediates for repurposing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If incineration at high temperatures is used to dispose of polyurethanes, then disposal efficiency is improved, but energy consumption and environmental impact increase

Engineering Contradiction:
Improvedisposal efficiencyVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent changes the chemical parameters of polyurethanes by incorporating degradable moieties (acetals, ketals, esters) that allow low-temperature degradation. This enables polyurethanes to be broken down at ambient or mild temperatures instead of requiring high-temperature incineration, thus reducing energy consumption while maintaining disposal efficiency through controlled chemical degradation pathways.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the mechanical/thermal system of high-temperature incineration with a chemical degradation system. By incorporating specific chemical functionalities (acetals, ketals, esters) into the polyurethane structure, the material undergoes chemical breakdown through hydrolysis or other chemical reactions under mild conditions, substituting the need for high-temperature thermal processing.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Ease of manufacture

If conventional polyurethane synthesis methods are used, then manufacturing simplicity is maintained, but sustainability and recyclability are compromised

Engineering Contradiction:
Improvemanufacturing simplicityVSAvoidsustainability
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent creates composite polyurethane materials by combining conventional polyurethane segments with degradable moieties (acetals, ketals, esters). This composite structure maintains the desirable properties of conventional polyurethanes while adding sustainability through built-in degradation pathways, allowing the material to be both easily manufactured and subsequently degraded for recycling or repurposing.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent incorporates degradable functionalities into the polyurethane structure during the synthesis stage, preparing the material in advance for future degradation. By including acetals, ketals, or esters that are predisposed to hydrolysis or chemical breakdown, the material is pre-equipped with degradation mechanisms that will activate when needed, enabling sustainable end-of-life management without complicating the initial manufacturing process.

Inventive Principle:
Principle #10Preliminary action

3Strength

If polyurethanes are designed for high durability, then product performance is improved, but degradability and circular economy compatibility are reduced

Engineering Contradiction:
ImprovedurabilityVSAvoiddegradability
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The patent segments the polyurethane structure into distinct functional zones: durable polyurethane segments that provide mechanical strength and stability, and degradable segments containing acetals, ketals, or esters that enable controlled breakdown. This segmented architecture allows different parts of the material to serve different functions - the polyurethane backbone maintains durability while the degradable moieties provide controlled degradation pathways for circular economy applications.

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 proposed solution allows for the controlled degradation of polyurethanes, reducing environmental impact and enabling the repurposing of degraded materials into new polymer products, thus promoting a circular economy.

Implementation Method 1

enabling acid-catalyzed degradation at room temperature and producing new hydroxy-functional polymer intermediates for repurposing

Methodology Applied
Scientific EffectAcid-catalyzed degradation: Catalysis

Data Source

PatentUS12338210B2Degradable polymers and monomers therefor
Publication Date: 2025.06.24 THE BOARD OF TRUSTEES OF THE UNIV OF ILLINOIS
  • US12338210B2 patent drawing
  • US12338210B2 patent drawing
  • US12338210B2 patent drawing

AI summary

Hydroxyacetal or hydroxyketal monomers, processes for their preparation, their use to produce degradable polymers, hydroxy-functional intermediates resulting from degradation, and repurposed polymers made from the hydroxy-functional intermediates are described. The invention avoids the energy-intensive conditions normally used to degrade polyurethanes and generates new hydroxy-functional intermediates that can be repurposed or upcycled. Polyurethanes and melamines, materials once destined for a landfill, can have a second life. Incorporation of a photoacid generator into microcapsule core materials and fabrication of the shell from the hydroxy-functional acetal or ketal monomers promotes facile, inside-out, solid-state degradation of the microcapsule shell triggered by UV light and acid generation in a hydrophobic environment. This enables controlled release of flavors, fragrances, biocides, agricultural actives, or other oil-based beneficial agents from within the microcapsules.