Cycloaliphatic Aldimine Mixture for Low-Isocyanate Polyurethane Strength

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Solution Overview

Problem

Elastic moisture-curing polyurethane compositions with low isocyanate content, particularly those based on cycloaliphatic isophorone diisocyanate, suffer from limited mechanical properties such as tensile strength and modulus of elasticity, and remain tacky under outdoor weathering conditions.

Innovation Solution

A mixture of isomeric cycloaliphatic aldimines with a specific isomer ratio of trans,trans to cis,trans and cis,cis in the range of 5/95 to 30/70, which are liquid at room temperature, is used to enhance the mechanical strength and elasticity of these compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If monomeric isophorone diisocyanate is removed from the isocyanate-functional polymer to reduce toxicity and volatility, then health and safety improve, but mechanical properties such as tensile strength and modulus of elasticity deteriorate

Engineering Contradiction:
Improvetoxicity and volatility of monomeric isocyanateVSAvoidtensile strength and modulus of elasticity
Core Design Contradiction:
Object-affected harmful factorsVSStrength

Solution Approach 1:

The invention changes the isomer composition parameter of the cycloaliphatic amine mixture, specifically maintaining a trans,trans isomer content between 30-70% in the aldimine mixture. This parameter optimization enables the system to achieve both low monomeric isocyanate content (<0.1 wt%) and improved mechanical properties, resolving the contradiction between health safety and mechanical strength

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses a composite approach by combining isocyanate-functional polymers with a specifically formulated mixture of isomeric cycloaliphatic aldimines. This composite system allows the polymeric isocyanate to provide mechanical strength while the controlled isomer mixture of aldimines enables proper curing, achieving both safety and performance requirements

Inventive Principle:
Principle #40Composite materials

2Strength

If non-monomeric isocyanates such as isophorone diisocyanate oligomers are added to compensate for low isocyanate content, then mechanical strength improves, but the cured composition becomes too stiff with reduced elongation

Engineering Contradiction:
Improvetensile strengthVSAvoidelongation and flexibility
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The invention optimizes the isomer composition parameter of the aldimine mixture, specifically controlling the trans,trans isomer content between 30-70%. This parameter control enables the system to achieve adequate tensile strength while maintaining high elongation (>200%), preventing the unwanted stiffening effect that occurs with conventional oligomeric isocyanates

Inventive Principle:
Principle #35Parameter changes

3Strength

If the isomer ratio of trans,trans to cis,trans and cis,cis is increased to improve mechanical strength, then tensile strength improves, but the composition becomes more prone to cracking and degradation

Engineering Contradiction:
Improvetensile strengthVSAvoidresistance to cracking and degradation
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The invention identifies and optimizes a specific parameter range for trans,trans isomer content (30-70%) in the aldimine mixture. This optimized parameter range achieves the optimal balance between mechanical strength and reliability, preventing both insufficient strength and excessive brittleness that lead to cracking and degradation under outdoor weathering 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 isomeric aldimine mixture improves tensile strength and modulus of elasticity, allowing for fast curing to non-tacky, elastic materials suitable for outdoor applications with high UV exposure and weather resistance, while maintaining low monomeric isocyanate content for safety.

Implementation Method 1

They react with isocyanate groups upon contact with moisture

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

react with isocyanate groups... improve the curing properties

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 3

the cycloaliphatic amine mixture from which the aldimine is derived, and the aldimine mixture itself, are liquid at room temperature

Methodology Applied
Scientific EffectPhase state:

Implementation Method 4

affords an improved mechanical strength to elastic coatings, sealants or adhesives... cure quickly to form elastic materials

Methodology Applied
Scientific EffectCuring reaction:

Data Source

PatentEP4229032B1Cycloaliphatic aldimine mixture
Publication Date: 2025.11.05 SIKA TECH AG
  • EP4229032B1 patent drawing
  • EP4229032B1 patent drawing
  • EP4229032B1 patent drawing

AI summary

The present invention describes a mixture of isomeric aldimines of the formulae (Ia), (Ib) and (Ic) in which the ratio of the trans,trans isomer (Ia) to the sum of the cis,trans isomer (Ib) and the cis,cis isomer (Ic) is in the range of 5/95 to 30/70, and its use as latent hardener for moisture-curing isocyanate-functional polyurethane compositions. The inventive mixture of isomeric aldimines enables polyurethane compositions with very low content of monomeric isophorone diisocyanate and excellent stability under outdoor wheathering conditions and high UV load, which cure quickly to an elastic material of low surface tack and good mechanical properties, particularly in terms of high tensile strength and modulus of elasticity at high elongation. Such compositions are particularly suitable as elastic adhesives and/or sealants or elastic coatings, particularly for outdoor use such as on roofs, floors or ships.