Alkylated Amine Epoxy Curing Agent Storage Stability

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Solution Overview

Problem

Amine compounds like meta-xylylenediamine are highly reactive, leading to storage stability issues due to carbonation when exposed to air, and have poor handleability due to low melting points, complicating their use as epoxy curing agents.

Innovation Solution

A method involving an addition reaction of ethylene and/or propylene with specific amine compounds in the presence of a base, using a base composition containing alkali metal compounds, to produce compounds with improved storage stability and handleability, suitable for use as epoxy curing agents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If amine compounds are stored in air atmosphere, then handling is simple, but storage stability deteriorates due to carbonation

Engineering Contradiction:
Improvehandling simplicityVSAvoidstorage stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent applies inert atmosphere by conducting the addition reaction in a nitrogen or argon atmosphere to prevent carbonation of the amine compound during storage and reaction, thereby maintaining storage stability while enabling simple handling without requiring complex protective measures

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

2Reliability

If amine compounds with low melting point are used, then reactivity is high, but handleability deteriorates due to crystallization at low temperatures

Engineering Contradiction:
ImprovereactivityVSAvoidhandleability
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent changes the physical parameters by conducting the reaction at controlled temperatures (0-10°C during ethylene filling, then raising to 20-40°C for reaction) and using specific pressure conditions (1.5-2.3 MPa ethylene filling pressure) to maintain the amine compound in a manageable state while preserving its high reactivity

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If additives are added to improve handleability, then handleability improves, but reaction purity deteriorates due to side reactants

Engineering Contradiction:
ImprovehandleabilityVSAvoidreaction purity
Core Design Contradiction:
Ease of operationVSManufacturing precision

Solution Approach 1:

The patent extracts and eliminates the need for additives by utilizing the amine compound itself and controlled reaction conditions (temperature and pressure parameters) to achieve both improved handleability and high reaction purity, removing harmful substances from the system

Inventive Principle:
Principle #2Taking out (Extraction)

4Reliability

If compounds reacting with carbon dioxide are used to improve storage stability, then storage stability improves, but reaction efficiency deteriorates due to reaction inhibition

Engineering Contradiction:
Improvestorage stabilityVSAvoidreaction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent uses inert atmosphere (nitrogen or argon) to create a protective environment that prevents carbonation during storage while not interfering with the intended addition reaction, thereby maintaining both storage stability and reaction efficiency without using compounds that would inhibit the reaction

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

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 produced compounds exhibit enhanced storage stability and handleability, allowing for their use as raw materials and intermediates in pharmaceuticals and agricultural chemicals, and as effective epoxy curing agents without the need for inert gas atmospheres or additives.

Implementation Method 1

subjecting a compound represented by Formula (5-1) to an addition reaction to add ethylene and/or propylene in the presence of a base

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3805197B1Method for producing compound, compound, epoxy curing agent, and method for producing amine composition
Publication Date: 2023.12.06 MITSUBISHI GAS CHEM CO INC
  • EP3805197B1 patent drawing
  • EP3805197B1 patent drawing
  • EP3805197B1 patent drawing

AI summary

Provided are: a method for producing a compound that excels in storage stability and handleability; the compound; and an epoxy curing agent containing the compound. The method for producing a compound represented by Formula (1-1) includes subjecting the compound represented by Formula (5-1) to an addition reaction to add ethylene and/or propylene in the presence of a base. In Formula (5-1), RX to RZ each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3. In Formula (1-1), RA to RD each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3.