Two-Component Curable Adhesive Composition with Aza-Michael Curing

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing adhesive technologies face challenges in achieving functional adhesive properties such as multi-substrate adhesion, stretchability, moldability, and self-healing, often requiring complex polymer structures and synthetic processes, while also dealing with issues like moisture sensitivity and catalyst requirements.

Innovation Solution

A two-component curable composition comprising a first component with (meth)acrylate groups and a second component with primary amine groups, along with a rheology control agent, allowing for aza-Michael addition reactions under mild conditions, which can form complex polymer structures without the need for complex synthetic processes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If complex polymer structures are used to achieve functional adhesive properties (multi-substrate adhesion, stretchability, moldability, self-healing), then adhesive performance is improved, but manufacturing complexity increases

Engineering Contradiction:
Improveadhesive performanceVSAvoidmanufacturing complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent changes the chemical parameters of the adhesive system by using aza-Michael addition reaction between amines and electron-deficient alkenes, which naturally forms complex polymer structures with desirable adhesive properties without requiring complex synthetic processes. The reaction conditions and stoichiometry are optimized to achieve the desired balance between adhesion, stretchability, and moldability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The aza-Michael addition reaction is self-curing, meaning the adhesive system automatically forms the complex polymer structure needed for functional adhesive properties through the chemical reaction between components, without requiring external catalysts or complex processing steps. The amine groups react with the electron-deficient alkene groups to form crosslinked networks that provide the required adhesive performance.

Inventive Principle:
Principle #25Self-service

2Reliability

If polyurethane adhesives are used to achieve excellent adhesion and environmental resistance, then adhesive performance is improved, but moisture sensitivity and catalyst control requirements increase

Engineering Contradiction:
Improveadhesive performanceVSAvoidmoisture sensitivity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition from polyurethane-based systems to aza-Michael addition systems, which use amine groups reacting with electron-deficient alkenes. This chemical parameter change eliminates the moisture sensitivity and catalyst control issues inherent in polyurethane systems while maintaining excellent adhesion and environmental resistance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent converts the typically harmful effect of moisture sensitivity in polyurethane systems into a benefit by using a chemical system (aza-Michael addition) that is inherently moisture-tolerant. The amine-based chemistry actually benefits from or is unaffected by moisture, eliminating the need for strict moisture control while maintaining adhesive performance.

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

3Reliability

If aza-Michael addition reaction is used to form complex polymer structures, then adhesive functionality is improved, but reaction temperature requirements may increase

Engineering Contradiction:
Improveadhesive functionalityVSAvoidreaction temperature
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent optimizes the temperature parameter of the aza-Michael addition reaction by selecting electron-deficient alkene groups that are highly reactive with amine groups, allowing the reaction to proceed at reduced temperatures. The chemical structure of the reactants is specifically chosen to lower the activation energy and enable curing at milder temperature 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 composition achieves dimensional stability and physical strength at temperatures below and above the glass transition temperature, demonstrating efficacious bonding properties and structural integrity.

Implementation Method 1

the present inventors have deemed aza-Michael addition - a conjugate addition reaction of an electrophilic electron acceptor with a reactant amine as the nucleophilic electron donor-to be a promising candidate process

Methodology Applied
Scientific EffectAza-Michael addition reaction: Chemical Bonding

Data Source

PatentEP4644474A1Two component (2K) curable adhesive composition
Publication Date: 2025.11.05 HENKEL KGAA
  • EP4644474A1 patent drawing
  • EP4644474A1 patent drawing
  • EP4644474A1 patent drawing

AI summary

A two-component (2K) curable composition comprising: a first component comprising: a) at least one compound having at least two (meth)acrylate groups and having a weight average molecular weight (Mw) of at most 600 Daltons; and, optionally b) at least one ethylenically unsaturated compound which is distinct from said compound(s) of a); and, a second component comprising: c) at least one compound having at least one primary amine group, wherein the two-component (2K) composition further comprises: d) a rheology control agent comprising electrically non-conductive fillers, electrically conductive fillers or mixtures thereof; and, further wherein the two-component (2K) composition is characterized in that the molar ratio of (meth)acrylate groups to primary amine groups is from 3:1 to 1:1.