Amine Compound for Epoxy Curing with Low Active Hydrogen Equivalent Weight

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Solution Overview

Problem

Epoxy resin curing agents with high active hydrogen equivalent weight (AHEW) require large amounts, increasing costs and limiting the blending composition, due to reduced active hydrogens in amine compounds after reaction with alkenyl compounds.

Innovation Solution

An amine compound with a specific structure, represented by formula (1), is synthesized through an addition reaction between a diamine and styrene in the presence of an alkali metal-containing catalyst, maintaining low AHEW and ensuring sufficient curability even at lower concentrations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If a polyamine is subjected to addition reaction with an alkenyl compound to reduce unreacted polyamine content and viscosity, then the curability decreases and active hydrogen equivalent weight increases, but if the AHEW is high, then a large amount of curing agent is required which increases cost and limits blending composition

Engineering Contradiction:
Improveactive hydrogen equivalent weightVSAvoidcurability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters of the amine compound by introducing specific cyclic structures (formula 1) with constrained geometry. This structural modification allows the compound to maintain a low active hydrogen equivalent weight (improving curability) while still achieving the desired reduction in unreacted polyamine content and viscosity through the addition reaction with alkenyl compounds.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the active hydrogen equivalent weight is increased to reduce the amount of curing agent needed, then the curability improves, but the blending composition becomes limited and cost increases

Engineering Contradiction:
ImprovecurabilityVSAvoidblending composition
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention modifies the molecular parameters of the amine compound by incorporating specific cyclic structures as defined in formula (1). These structural changes enable the compound to achieve low AHEW values that improve curability while maintaining compatibility with various epoxy resin systems, thus expanding rather than limiting blending composition options.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If the amount of epoxy resin curing agent is increased to ensure sufficient curability, then the curability is sufficient, but the cost increases and blending composition is limited

Engineering Contradiction:
ImprovecurabilityVSAvoidamount of curing agent
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The invention changes the fundamental parameters of the amine compound structure (formula 1) to achieve a low active hydrogen equivalent weight. This allows the curing agent to be used in smaller amounts while still providing sufficient curability, thereby reducing both the quantity of curing agent needed and the associated costs.

Inventive Principle:
Principle #35Parameter changes

4Ease of operation

If a polyamine is reacted with an alkenyl compound to reduce viscosity and unreacted polyamine content, then the epoxy resin composition properties improve, but the active hydrogen equivalent weight increases reducing curability

Engineering Contradiction:
ImproveviscosityVSAvoidcurability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The invention introduces specific structural parameters in the amine compound (formula 1) that allow it to achieve low viscosity and low unreacted polyamine content through addition reaction, while simultaneously maintaining a low active hydrogen equivalent weight that ensures good curability. The cyclic structure in formula (1) is key to achieving this multi-parameter optimization.

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 amine compound and composition provide excellent curability and properties in epoxy resin compositions, suitable for various applications like corrosion-resistant paints and adhesives, with reduced material usage and cost.

Implementation Method 1

an amine compound obtained by subjecting a polyamine and an alkenyl compound to addition reaction

Methodology Applied
Scientific EffectAddition reaction: Chemical Bonding

Implementation Method 2

subjecting a diamine and styrene to addition reaction in the presence of an alkali metal-containing catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10941242B2Amine compound, amine composition, and epoxy resin curing agent
Publication Date: 2021.03.09 MITSUBISHI GAS CHEM CO INC
  • US10941242B2 patent drawing
  • US10941242B2 patent drawing
  • US10941242B2 patent drawing

AI summary

Provided are an amine compound represented by the following formula (1), which has a low active hydrogen equivalent weight and thus is capable of providing a cured product having good properties because the amine compound has sufficient curability even though the amount of amine compound blended in an epoxy resin composition is small when the amine compound is used as an epoxy resin curing agent, and an amine composition and an epoxy resin curing agent, which contain the compound:wherein A is a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group.