Alpha-Type Tris-Epoxy Isocyanurate Crystal Solubility

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Solution Overview

Problem

Common tris-(2,3-epoxypropyl)-isocyanurate compositions have limited solubility and stability issues due to the presence of β-type crystals, leading to precipitation during storage and restricted applicability.

Innovation Solution

Producing an α-type tris-(2,3-epoxypropyl)-isocyanurate crystal with a controlled ratio of β-type tris-(2,3-epoxypropyl)-isocyanurate (2% to 15% by weight) and optimizing particle size (1 to 500 μm) to enhance solubility and storage stability, using methods such as solid-liquid separation and solvent extraction.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If common tris-(2,3-epoxypropyl)-isocyanurate containing 25% β-type crystal is used, then the cured product has excellent transparency and heat resistance, but the solubility is significantly low and crystal precipitates during storage

Engineering Contradiction:

Improvestorage stabilityVSAvoidsolubility

Core Design Contradiction:

ReliabilityVSEase of operation

Solution Approach 1:

The invention changes the crystal form parameter from β-type to α-type, which fundamentally alters the solubility characteristics while maintaining the curing performance. The α-type crystal has a different molecular packing arrangement that enables significantly higher solubility in liquid carboxylic acid anhydrides compared to the β-type crystal.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention introduces a localized structural modification by controlling the crystal lattice arrangement to form α-type structure with specific spatial configuration of the isocyanurate ring and epoxy groups, which creates favorable interaction sites for solvent molecules while preserving the overall molecular structure needed for curing.

Inventive Principle:

Principle #3Local quality

2Temperature

If β-type tris-(2,3-epoxypropyl)-isocyanurate crystal is used, then the melting point is high (about 150°C), but the solubility to various solvents is significantly low

Engineering Contradiction:

Improvemelting pointVSAvoidsolubility

Core Design Contradiction:

TemperatureVSEase of operation

Solution Approach 1:

Inventive Principle:

Principle #35Parameter changes

3Stability of the object's composition

If common tris-(2,3-epoxypropyl)-isocyanurate is dissolved with solvent, then a homogenous composition can be formed, but crystal precipitates over time during storage

Engineering Contradiction:

Improvecomposition homogeneityVSAvoidstorage period

Core Design Contradiction:

Stability of the object's compositionVSDuration of action of stationary object

Solution Approach 1:

The invention changes the crystal form from β-type to α-type, which has different solubility characteristics that prevent precipitation during storage. The α-type crystal's molecular arrangement allows for better solvent interaction and maintains composition homogeneity over extended storage periods.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention performs preliminary crystal form selection by using α-type crystal before forming the composition, which preemptively prevents the precipitation issue that would occur during storage, ensuring long-term stability without requiring additional stabilizing measures.

Inventive Principle:

Principle #10Preliminary action

4Adaptability or versatility

If limited liquid carboxylic acid anhydrides are used to dissolve common tris-(2,3-epoxypropyl)-isocyanurate, then the composition can be formed, but the applicable range is limited and the composition cannot be stored

Engineering Contradiction:

Improveapplicable rangeVSAvoidstorage stability

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The invention changes the crystal form to α-type, which expands the applicable range of liquid carboxylic acid anhydrides that can be used as solvents. This crystal form modification enables compatibility with a broader spectrum of curing agents while simultaneously providing storage stability.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The α-type tris-(2,3-epoxypropyl)-isocyanurate crystal serves multiple functions: it provides excellent solubility in various liquid carboxylic acid anhydrides, maintains composition homogeneity during storage, and delivers the required curing performance, making it a universal solution for different application requirements.

Inventive Principle:

Principle #6Universality (Multi-functionality)

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 α-type tris-(2,3-epoxypropyl)-isocyanurate crystal exhibits high solubility, stability, and compatibility with curing agents, enabling the formation of homogeneous compositions that can be stored long-term and cured into products with excellent transparency, heat resistance, and light resistance.

Implementation Method 1

separating β-type tris-(2,3-epoxypropyl)-isocyanurate contained in a tris-(2,3-epoxypropyl)-isocyanurate solution from the solution as a solid to obtain a crystal with an increased content ratio of α-type tris-(2,3-epoxypropyl)-isocyanurate

Methodology Applied

Scientific EffectSolid-liquid separation: Sedimentation

Implementation Method 2

extracting β-type tris-(2,3-epoxypropyl)-isocyanurate contained in the crystal or the solution obtained in (i) with a solvent to obtain a crystal with an increased content ratio of α-type tris-(2,3-epoxypropyl)-isocyanurate

Methodology Applied

Scientific EffectSolvent extraction: Liquid-Liquid Extraction

Data Source

PatentUS12091506B2Highly soluble tris-(2, 3-epoxypropyl)-isocyanurate and method for producing same

Publication Date: 2024.09.17 NISSAN CHEM CORP

AI summary

There is provided an epoxy composition which has difficulty in precipitating a crystal during storage, is homogeneous and can be stored for a long period; and a cured product of the composition having excellent transparency, heat resistance, and light resistance can be obtained on curing. An α-type tris-(2,3-epoxypropyl)-isocyanurate crystal including β-type tris-(2,3-epoxypropyl)-isocyanurate in the crystal in a ratio of 2% by mass to 15% by mass. A method for producing the α-type tris-(2,3-epoxypropyl)-isocyanurate crystal including step (i) separating β-type tris-(2,3-epoxypropyl)-isocyanurate contained in a tris-(2,3-epoxypropyl)-isocyanurate solution from the solution as a solid to obtain a crystal with an increased content ratio of α-type tris-(2,3-epoxypropyl)-isocyanurate.