Epoxy Resin Curing Agent Composition for Low Viscosity and Water Resistance

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Solution Overview

Problem

Existing epoxy resin compositions using polyamine compounds as curing agents suffer from high viscosity and reduced water resistance due to amine blushing, leading to sticky surfaces and compromised coating performance.

Innovation Solution

A modified amino compound derived from a predetermined aliphatic diamine, such as bis(aminomethyl)cyclohexane, is synthesized through a reaction with an aldehyde compound followed by reduction, resulting in a low-viscosity epoxy resin curing agent that forms coatings with enhanced water resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a polyamine compound such as bis(aminomethyl)cyclohexane is used as an epoxy resin curing agent, then the coating film exhibits excellent weather resistance and fast curing at room temperature, but amine blushing occurs on the surface making it sticky and reducing water resistance

Engineering Contradiction:
Improveweather resistanceVSAvoidamine blushing and reduced water resistance
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention modifies the chemical structure of the polyamine compound by introducing specific cyclic groups and controlling the ratio of primary to secondary amino groups (where the ratio of primary amino groups is 0.05 to 2.0 mol/mol of secondary amino groups). This structural parameter change eliminates amine blushing while maintaining fast curing and weather resistance properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The curing agent combines multiple functional groups within a single molecular structure - cyclic groups for structural stability, primary amino groups for reactivity and crosslinking, and secondary amino groups for controlled curing rate. This composite molecular structure achieves both fast curing and excellent water resistance without amine blushing.

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If modified products of polyamine are used as epoxy resin curing agents to improve water resistance, then water resistance is enhanced, but the viscosity becomes high

Engineering Contradiction:
Improvewater resistanceVSAvoidviscosity
Core Design Contradiction:
Object-affected harmful factorsVSEase of operation

Solution Approach 1:

The invention carefully controls the molecular weight and structural complexity of the modified polyamine by limiting the types of cyclic groups introduced and controlling the amino group ratios. This parameter optimization maintains low viscosity for easy application while achieving excellent water resistance through the engineered molecular structure.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If non-reactive diluents are added to reduce viscosity of modified polyamine curing agents, then viscosity is reduced, but water resistance is compromised

Engineering Contradiction:
ImproveviscosityVSAvoidwater resistance
Core Design Contradiction:
Ease of operationVSObject-affected harmful factors

Solution Approach 1:

Instead of using non-reactive diluents that temporarily reduce viscosity but compromise water resistance, the invention designs the curing agent molecule itself to have appropriate fluidity through controlled molecular structure. The molecule acts as its own vehicle, eliminating the need for sacrificial diluents that would harm water resistance.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 amino compound achieves low viscosity and forms coatings with excellent water resistance, improving the durability and appearance of epoxy resin films without the need for non-reactive diluents.

Implementation Method 1

reacting a diamine represented by the following general formula (5) and an aldehyde compound represented by the following general formula (6) to obtain an imine

Methodology Applied
Scientific EffectCondensation reaction:

Implementation Method 2

the step of reducing the imine obtained in the step (1)

Methodology Applied
Scientific EffectReduction: Reduction

Data Source

PatentUS20260022104A1Amino compound and method for producing same, epoxy resin curing agent, and epoxy resin composition and cured product of same
Publication Date: 2026.01.22 MITSUBISHI GAS CHEM CO INC
  • US20260022104A1 patent drawing
  • US20260022104A1 patent drawing
  • US20260022104A1 patent drawing

AI summary

An amino compound represented by formula (1) and a method for producing the same, an epoxy resin curing agent containing the amino compound, an epoxy resin composition, and a cured product thereof: R1—NH—X—NH—R2 (1) wherein R1 and R2 are each independently a hydrogen atom or a monovalent group represented by formula (2), at least one of R1 and R2 is a monovalent group represented by formula (2), X is a divalent group represented by —CH2—A—CH2— (A is a cyclohexylene group), —(CH2)n—, —(CH2CH2NH)m—CH2CH2—, or a divalent group represented by formula (3) or (4), n is 2 to 6, and m is 1 or 2,wherein a dashed line indicates presence or absence of a π bond, R3 to R5 are each independently a hydrogen atom or an alkyl group that has 1 to 4 carbon atoms and optionally has a hydroxy group, and * represents a bonding position