Amine-functional curing agents for epoxy coatings

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Solution Overview

Problem

Amine-functional curing agents for epoxy-functional compounds face issues such as skin sensitization, environmental sensitivity, and the formation of 'amine-bloom' due to reactions with water and CO2, leading to adverse film properties and health concerns, especially at low temperatures and high humidity.

Innovation Solution

The development of amine-functional curing agents formed by reacting mono-functional epoxy compounds with amides derived from α-β unsaturated acids or esters, which are stable and resistant to amine bloom, allowing for high solids content coatings with improved color stability and curing rates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If amine-functional compounds are used to cure epoxy-functional compounds, then the curing reaction proceeds effectively, but the system becomes sensitive to environmental conditions (humidity and CO2) leading to amine-bloom formation

Engineering Contradiction:
Improvecuring reaction efficiencyVSAvoidstability under environmental conditions
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies preliminary action by pre-reacting the amine-functional compound with a carboxylic acid or ester to form an amide bond before the epoxy curing process. This pre-reaction reduces the free amine content that would otherwise react with environmental moisture and CO2, thereby preventing amine-bloom formation while maintaining curing effectiveness through the retained amine groups

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent changes the chemical parameter of the curing agent by introducing amide groups through reaction with carboxylic acids or esters. This modification alters the reactivity and environmental stability of the amine groups, reducing their sensitivity to humidity and CO2 while preserving their epoxy-curing capability

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If the molecular weight of the amine-functional compound is increased to reduce skin sensitization risk, then safety improves, but the viscosity increases requiring more solvent

Engineering Contradiction:
Improveskin sensitization riskVSAvoidsolvent content
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent changes the chemical structure parameter by introducing amide groups through reaction with carboxylic acids or esters. This structural modification increases molecular weight and reduces skin sensitization risk while the specific chemistry maintains relatively low viscosity, reducing the need for excessive solvent addition

Inventive Principle:
Principle #35Parameter changes

3Use of energy by moving object

If low temperature curing is performed, then energy consumption decreases, but amine-bloom formation increases due to higher reactivity with water and CO2

Engineering Contradiction:
Improvecuring energy consumptionVSAvoidamine-bloom formation
Core Design Contradiction:
Use of energy by moving objectVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary action by pre-forming amide bonds before low-temperature curing. This reduces the population of free amine groups available to react with environmental moisture and CO2 during low-temperature curing, thereby preventing amine-bloom formation while maintaining the energy efficiency of low-temperature processing

Inventive Principle:
Principle #10Preliminary action

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

These agents prevent amine bloom formation, reduce the need for organic solvents, and provide coatings with enhanced color stability and curing efficiency, even at low temperatures and high humidity, while minimizing health and environmental risks.

Implementation Method 1

the amine-functional curing agent can react with water and CO 2 to form carbamate salts

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

there are fewer amine groups to react with epoxy groups. This has an effect on the network that is formed in the film

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP1973959B1Curing agents for epoxy-functional compounds
Publication Date: 2018.08.08 AKZO NOBEL COATINGS INT BV

AI summary

The present invention relates to compounds suitable to use as curing agents for epoxy systems which can be obtained by reacting an amine-functional compound with an a-ß unsaturated acid and/or ester and a mono-functional epoxy compound. The invention further relates to coating compositions comprising these curing agents.