Stabilizing Isocyanate Unsaturated Compounds

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Solution Overview

Problem

Ethylenically unsaturated compounds with isocyanate groups are prone to polymerization, multimerization, and discoloration reactions, leading to production inefficiencies, product degradation, and economic losses due to solid formation and quality issues during processing and storage.

Innovation Solution

Incorporating a stabilizing agent, such as 3'-chloro-2'-methylpropionyl-2-oxyethyl isocyanate, into the isocyanate group-containing ethylenically unsaturated compounds to replace ethylenically unsaturated groups with alkyl halide or amino alkyl groups, which helps prevent polymerization and multimerization reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If various solid polymerization inhibitors are added to prevent polymerization, then polymerization is suppressed to some extent, but the prevention effect is insufficient and additional complex methods are required

Engineering Contradiction:
Improvepolymerization prevention effectVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention changes the chemical structure parameter by introducing a specific stabilizing agent with a chlorinated alkyl group that reacts with the isocyanate group to form a stable cyclic structure, fundamentally altering the reactivity parameters of the system to achieve effective polymerization prevention

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The stabilizing agent acts as an intermediary substance that reacts with the isocyanate group to form a cyclic structure, mediating between the isocyanate compound and the polymerization process to prevent unwanted reactions while maintaining product functionality

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If the ethylenically unsaturated compound is stored for later use, then production flexibility is improved, but multimerization reactions occur causing cloudiness and discoloration

Engineering Contradiction:
Improveproduction flexibilityVSAvoidproduct quality stability
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The stabilizing agent is introduced into the system before storage occurs, performing a preliminary stabilization action by forming a cyclic structure with the isocyanate group that prevents multimerization reactions during subsequent storage periods

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The stabilizing agent performs preliminary anti-action by pre-reacting with the isocyanate group to form a stable cyclic structure, thereby preventing the multimerization reaction from occurring during storage rather than addressing it after it begins

Inventive Principle:
Principle #9Preliminary anti-action

3Manufacturing precision

If the compound is heated to remove impurities, then purification is improved, but polymerization occurs forming solids that clog facilities

Engineering Contradiction:
Improvepurification qualityVSAvoidsolid formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The invention converts the potentially harmful effect of heat into a beneficial stabilization process, where the stabilizing agent reacts with the isocyanate group during heating to form a stable cyclic structure, transforming the heat-induced polymerization risk into an opportunity for stabilization

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

4Reliability

If alcohol or (meth)acrylic acid is added to prevent polymerization, then some polymerization inhibition is achieved, but the method is less effective and causes functional adverse effects

Engineering Contradiction:
Improvepolymerization inhibitionVSAvoidfunctional adverse effects
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the chemical parameter by using a chlorinated alkyl group instead of alcohol or carboxylic acid, which fundamentally alters the reaction mechanism to form a stable cyclic structure without the functional adverse effects associated with conventional inhibitors

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The stabilizing agent serves as a temporary, disposable substance that reacts with the isocyanate group to form a stable cyclic structure, providing effective polymerization prevention without the long-term functional issues caused by conventional inhibitors like alcohol or acrylic acid

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

Effectively stabilizes the isocyanate group-containing ethylenically unsaturated compounds, preventing the generation of impurities, cloudiness, discoloration, and purity reduction, thereby enhancing production efficiency and maintaining product quality.

Implementation Method 1

a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl halide group or an amino alkyl group

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentEP2676950B1Stabilized isocyanate group-containing ethylene-based unsaturated compound
Publication Date: 2018.04.18 RESONAC HOLDINGS CORP

AI summary

An object of the present invention is to improve the stability of an ethylenically unsaturated compound having an isocyanate group in the molecule by preventing a polymerization, a multimerization reaction and a discoloration reaction of the ethylenically unsaturated compound. The present invention relates to a stabilizing composition for an isocyanate group-containing ethylenically unsaturated compound, comprising: an isocyanate group-containing ethylenically unsaturated compound (A) which comprises one or more isocyanate groups and one or more ethylenically unsaturated groups in the molecule; and a stabilizing agent (B) which is a compound in which at least one of the ethylenically unsaturated groups in the compound (A) is replaced with an alkyl halide group or an amino alkyl group which may have a substituent.