Polyisocyanate Composition with Controlled Trans Isomer Content

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Solution Overview

Problem

Current polyurethane resin production methods do not adequately tailor physical properties for various applications, limiting the versatility and performance of resulting materials.

Innovation Solution

The use of 1,4-bis(isocyanatomethyl)cyclohexane with a specific trans isomer content and a compound represented by formula (1) in a polyisocyanate composition, which includes functional groups such as isocyanurate, allophanate, biuret, urethane, and urea groups, to produce a polyurethane resin with enhanced physical properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If conventional polyisocyanate compositions are used, then production process is simple, but physical properties of polyurethane resin cannot be optimized for various applications

Engineering Contradiction:
Improvephysical properties optimizationVSAvoidproduction process complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by precisely controlling the trans isomer content (70-95 mol%) and the compound of formula (1) content (0.1-300 ppm) in the 1,4-bis(isocyanatomethyl)cyclohexane. This optimization of compositional parameters enables the polyurethane resin to achieve excellent physical properties including high strength, elasticity, and durability while maintaining a feasible production process

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material principles by creating a polyisocyanate composition that integrates 1,4-bis(isocyanatomethyl)cyclohexane with specific isomer ratios and controlled impurity levels as a compound material. This composite approach allows the resulting polyurethane resin to exhibit synergistic properties combining strength, elasticity, and processability that cannot be achieved with single components

Inventive Principle:
Principle #40Composite materials

2Strength

If trans isomer content is increased to improve physical properties, then resin performance improves, but manufacturing precision requirements increase

Engineering Contradiction:
Improvepolyurethane resin strengthVSAvoidisomer ratio control precision
Core Design Contradiction:
StrengthVSManufacturing precision

Solution Approach 1:

The patent resolves this contradiction by defining an optimal parameter range for trans isomer content (70-95 mol%) rather than requiring a single precise value. This range optimization allows sufficient flexibility in manufacturing while ensuring the polyurethane resin achieves the required strength and physical properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses compound (1) as a marker or copy indicator to monitor and control the isomer composition. By measuring the content of this specific compound within the range of 0.1-300 ppm, manufacturers can indirectly control the trans isomer ratio and ensure consistent resin quality without requiring direct measurement of each isomer

Inventive Principle:
Principle #26Copying

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

This approach enables the production of polyurethane resins with improved physical properties, suitable for a range of applications, including fibers, films, and molded articles, by optimizing the trans isomer content and functional group distribution in the polyisocyanate composition.

Implementation Method 1

A polyurethane resin of the present invention is produced by allowing a polyisocyanate component containing the above-described 1,4-bis(isocyanatomethyl)cyclohexane to react with an active hydrogen group-containing component

Methodology Applied
Scientific EffectPolymerization reaction: Chemical Bonding

Data Source

PatentEP3037411B11,4-bis(isocyanatomethyl)cyclohexane, polyisocyanate composition, polyurethane resin, molded article, eyewear material, eyewear frame and lens
Publication Date: 2019.03.27 MITSUI CHEMICALS INC
  • EP3037411B1 patent drawingFigure 1
  • EP3037411B1 patent drawingFigure 2
  • EP3037411B1 patent drawingFigure 3

AI summary

1,4-bis(isocyanatomethyl)cyclohexane contains 70 mol% or more and 95 mol% or less of a trans isomer relative to a total amount of a cis isomer and the trans isomer, and 0.1 ppm or more and 300 ppm or less of the compound represented by formula (1) below: