Moisture-Curing Polyurethane Composition with Aldimine Hardening

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Solution Overview

Problem

Moisture-curing polyurethane compositions with low monomeric isophorone diisocyanate content suffer from surface tackiness and limited mechanical strength, particularly under outdoor weathering conditions, and pose health risks due to the toxicity of monomeric isophorone diisocyanate.

Innovation Solution

A moisture-curing polyurethane composition with a low content of monomeric isophorone diisocyanate, using an aldimine of formula (I) to form elastic materials with improved mechanical strength and reduced tackiness, suitable for outdoor applications.

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, then health safety is improved, but mechanical strength and surface tackiness deteriorate

Engineering Contradiction:
Improvetoxicity of monomeric isophorone diisocyanateVSAvoidmechanical strength
Core Design Contradiction:
Object-affected harmful factorsVSStrength

Solution Approach 1:

The patent removes monomeric isophorone diisocyanate from the isocyanate-functional polymer through distillation to eliminate toxicity, then compensates for the resulting mechanical strength loss by adding oligomeric isophorone diisocyanate crosslinkers and specific aldimines as latent hardeners

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the molecular weight distribution of isocyanate compounds by replacing monomeric IPDI with oligomeric IPDI crosslinkers, thereby maintaining crosslinking density and mechanical strength while reducing toxicity from the monomeric form

Inventive Principle:
Principle #35Parameter changes

2Strength

If oligomeric isophorone diisocyanate crosslinkers are added to compensate for mechanical strength, then mechanical strength is improved, but elongation and flexibility deteriorate due to stiffening

Engineering Contradiction:
Improvemechanical strengthVSAvoidelongation and flexibility
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The patent optimizes the molecular weight and functionality of oligomeric IPDI crosslinkers to achieve sufficient mechanical strength while maintaining elongation above 200%, and controls the NCO content and aldimine ratio to balance crosslinking density with flexibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite curing system combining oligomeric IPDI crosslinkers with specific aldimines (N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-4,4'-methylene-bis(cyclohexylamine)) to achieve synergistic effects that maintain both strength and elasticity

Inventive Principle:
Principle #40Composite materials

3Object-affected harmful factors

If isocyanate content is reduced to lower toxicity, then health safety is improved, but UV resistance and mechanical performance deteriorate

Engineering Contradiction:
ImprovetoxicityVSAvoidUV resistance
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent uses isocyanate-functional polymers with controlled NCO content (1-10 wt%) and replaces monomeric IPDI with oligomeric IPDI, maintaining UV resistance through the isophorone diisocyanate-based polymer structure while reducing toxicity by eliminating monomeric IPDI through distillation

Inventive Principle:
Principle #35Parameter changes

4Reliability

If aldimines are used as latent hardeners to improve curing properties, then bubble formation is prevented, but surface tackiness increases

Engineering Contradiction:
Improvebubble formation preventionVSAvoidsurface tackiness
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent selects specific aldimines with controlled molecular weight and structure (N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-4,4'-methylene-bis(cyclohexylamine)) and optimizes their content (0.1-10 wt%) to achieve complete curing with minimal surface tackiness while maintaining bubble formation prevention

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 composition achieves fast curing with low surface tackiness, high mechanical strength, and durability under UV and water exposure, while maintaining low viscosity and shelf life stability, suitable for outdoor coatings and sealants.

Implementation Method 1

They react with isocyanate groups upon contact with moisture

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

aldimines serve as so-called latent hardeners or blocked amines. They react with isocyanate groups

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 3

good UV resistance... durability under UV and water exposure

Methodology Applied
Scientific EffectPhotopolymerisation: Photopolymerisation

Data Source

PatentEP4229031B1Moisture-curing polyurethane composition
Publication Date: 2025.11.05 SIKA TECH AG
  • EP4229031B1 patent drawing
  • EP4229031B1 patent drawing
  • EP4229031B1 patent drawing

AI summary

The present invention describes a moisture-curing polyurethane composition comprising – at least one isocyanate-functional polymer with a content of monomeric isophorone diisocyanate of below 0.5 weight-%, obtained from the reaction of isophorone diisocyanate and at least one polyol, and – at least one aldimine of the formula (I). The composition has a low toxicity, a good shelf life stability and cures 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. It enables coatings, sealants and adhesives with excellent stability under outdoor wheathering conditions and high UV load. The aldimine of the formula (I) allows to overcome the drawbacks caused by the removal of most of the monomeric isophorone diisocyanate in terms of cure speed, surface tackyness and final strength of such compositions. The inventive compositions are particularly suitable as elastic adhesives and/or sealants or elastic coatings, particularly for outdoor use such as on roofs, floors or ships.