Diisocyanate Trimerization via High-Boiling Solvent Extraction

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Solution Overview

Problem

The existing methods for producing isocyanurates from volatile and moderately volatile diisocyanates require costly and inconvenient distillative removal of excess monomeric diisocyanates, leading to thermal stress and residual non-light-stable aromatic components in the end product.

Innovation Solution

Using diisocyanates with a boiling point above 350°C as solvents to trimerize volatile and moderately volatile diisocyanates, with a trimerization catalyst, to achieve a composition where at least 60% of the volatile diisocyanates are converted to trimers or oligomers, thereby eliminating the need for distillative removal.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If distillative removal of excess monomeric diisocyanate is performed, then the proportion of residual monomers is reduced, but the process becomes costly and inconvenient with additional apparatus complexity and thermal stress

Engineering Contradiction:
Improveresidual monomer contentVSAvoiddistillation apparatus
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The harmful component (monomeric diisocyanate) is extracted from the reaction mixture by forming a percolate layer that selectively contains the monomer, allowing its removal without complex distillation apparatus

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The solubility parameters are changed by selecting a percolate component whose solubility in the reaction mixture is between that of the monomeric diisocyanate and the trimer/oligomer, enabling selective separation based on solubility differences rather than requiring thermal distillation

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If distillation is used to remove monomeric diisocyanate, then residual monomer content is reduced, but thermal stress alters the product causing discolouration

Engineering Contradiction:
Improveresidual monomer contentVSAvoidproduct discolouration
Core Design Contradiction:
Manufacturing precisionVSObject-affected harmful factors

Solution Approach 1:

The mechanical/thermal distillation system is replaced with a solubility-based liquid-liquid extraction system using a percolate component, eliminating thermal stress that causes product discolouration while still achieving monomer removal

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Ease of manufacture

If aromatic isocyanates are used in mixed trimerization, then the process is simplified, but non-light-stable aromatic components remain in the end product

Engineering Contradiction:
Improvetrimerization processVSAvoidlight stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The percolate component is specifically selected to have solubility characteristics that enable it to preferentially dissolve aromatic monomeric isocyanates while leaving the trimer/oligomer phase unaffected, providing targeted removal of light-unstable components

Inventive Principle:
Principle #3Local quality

4Productivity

If monoalcohol is used as cocatalyst in trimerization, then the reaction proceeds, but functionality and NCO content are reduced and inhibitors must be added

Engineering Contradiction:
Improvetrimerization reaction rateVSAvoidfunctionality and NCO content
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The percolate component extracts and removes the alcohol cocatalyst along with the monomeric isocyanate from the reaction mixture, restoring the full functionality and NCO content of the trimer/oligomer product without requiring inhibitor addition

Inventive Principle:
Principle #2Taking out (Extraction)

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 process reduces the residual monomer content to less than 20% by weight, enhancing the stability and usability of the end product while avoiding thermal stress and the use of distillation, thus improving the industrial viability and safety by minimizing hazardous diisocyanate release.

Implementation Method 1

Using diisocyanates with a boiling point above 350°C as solvents to trimerize volatile and moderately volatile diisocyanates

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

with a trimerization catalyst, to achieve a composition where at least 60% of the volatile diisocyanates are converted to trimers or oligomers

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10793664B2Process for preparing trimers and/or oligomers of diisocyanates
Publication Date: 2020.10.06 EVONIK OPERATIONS GMBH

AI summary

A process for preparing trimers and/or oligomers of diisocyanates is disclosed along with a composition of trimers and/or oligomers formed from diisocyanates and monomeric diisocyanates obtainable by reaction of I. 5-94.999% by weight of A) at least one diisocyanate having a boiling point of less than 250° C. (at standard pressure) and/orB) at least one diisocyanate having a boiling point of 250-350° C. (at standard pressure), in the presence of II. 94.999-5% by weight ofC) at least one diisocyanate having a boiling point above 350° C. (at standard pressure), III. in the presence of at least one trimerization catalyst in amounts of 0.001% to 5% by weight, and the amounts of I.-III. add up to 100% by weight.