Poly(Urea-Urethane) HUB Recycling for Reprocessable Composites

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Solution Overview

Problem

There is a need for polymeric materials with desired in-use performance characteristics that are malleable, repairable, and shape reprogrammable, and for recycling methods that can degrade or reversibly depolymerize these materials, particularly for composite materials like glass fiber reinforced plastics (GFRP) that are difficult to recycle due to their thermoset nature.

Innovation Solution

A process for recycling poly(urea-urethane) polymers by treating them under conditions to partially cleave urea bonds, forming a mixture of prepolymers, which can be reshaped or repaired, using dynamic hindered urea bonds (HUBs) that act as covalent adaptable networks (CANs), allowing for thermo-mechanical processing and recovery of valuable materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional thermosets are used to provide dimensional stability and chemical resistance, then mechanical performance and stability are improved, but recyclability and reprocessability deteriorate

Engineering Contradiction:
Improvedimensional stability and chemical resistanceVSAvoidrecyclability and reprocessability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies dynamic covalent chemistry by incorporating reversible imine bonds and disulfide bonds into the polymer network. These dynamic bonds allow the thermoset to undergo bond exchange reactions under specific conditions (pH, temperature), enabling the material to transition from a rigid, non-reprocessable state to a flexible, reprocessable state. This resolves the contradiction by making the previously static network dynamically adaptable.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent changes the chemical parameters of the polymer network by introducing functional groups that can undergo reversible reactions. The imine bonds can form and break under different pH conditions, and disulfide bonds can exchange under specific temperature and catalytic conditions. These parameter changes enable the material to switch between stable and reprocessable states, simultaneously achieving reliability and recyclability.

Inventive Principle:
Principle #35Parameter changes

2Strength

If thermoset polymers are used to achieve excellent mechanical performance, then strength and stability are improved, but adaptability and reshaping capability deteriorate

Engineering Contradiction:
Improvemechanical performanceVSAvoidreshaping and reprocessing capability
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The patent introduces dynamic covalent bonds (imine and disulfide) that can reversibly break and reform under specific conditions. This dynamic behavior allows the material to maintain structural integrity during use (providing strength) while enabling reshaping and reprocessing when exposed to triggering conditions such as pH changes or temperature variations.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent employs periodic or triggered actions to initiate bond exchange reactions. By applying specific stimuli (pH changes, temperature cycles, catalytic agents) at appropriate times, the material can periodically transition between stable and reprocessable states, enabling controlled reshaping while maintaining overall structural performance.

Inventive Principle:
Principle #19Periodic action

3Strength

If poly(urea-urethane) polymers with hindered urea bonds are used to provide desired in-use performance, then mechanical characteristics are improved, but degradability and depolymerization capability deteriorate

Engineering Contradiction:
Improvein-use performance characteristicsVSAvoiddegradability and depolymerization time
Core Design Contradiction:
StrengthVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical environment parameters (pH, temperature, presence of catalysts) to trigger the depolymerization of hindered urea bonds. Under specific conditions such as acidic or basic environments, the urea bonds undergo hydrolysis or exchange reactions that break down the polymer network, enabling controlled degradation and depolymerization while maintaining mechanical performance under normal use conditions.

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 process enables the recovery and reuse of poly(urea-urethane) polymers and fillers like carbon fibers, facilitating easy repairability and recyclability, while reducing waste and carbon footprint, and providing materials suitable for various applications.

Implementation Method 1

treatment of the composition comprising the poly(urea-urethane) polymer under conditions suitable to at least partially cleave the urea bonds of the polymer

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

urea bonds bearing a bulky group on the nitrogen atom resulted in hindered urea bonds (HUBs) that were dynamic and can reversibly dissociate into an amine and isocyanate based on the associative exchange mechanisms

Methodology Applied
Scientific EffectAssociative exchange mechanism: Chemical Bonding

Data Source

PatentUS20260049171A1Closed loop recycling concept for composites comprising covalent adaptable poly(urea-urethane) networks with dynamic hindered urea bonds
Publication Date: 2026.02.19 BASF SE
  • US20260049171A1 patent drawing
  • US20260049171A1 patent drawing
  • US20260049171A1 patent drawing

AI summary

The present invention relates to a process for recycling a composition comprising a poly(urea-urethane) polymer with hindered urea bonds comprising the treatment of the composition comprising the poly(urea-urethane) polymer under conditions suitable to at least partially cleave the urea bonds of the polymer to give a mixture (M1) containing prepolymers. The present invention also relates to the prepolymer obtained or obtainable according to the process, a poly(urea-urethane) polymer obtained or obtainable according to the process according to the present invention as well as the use of said prepolymer for the preparation of a poly(urea-urethane) polymer.