Reactive Urethane Compound with Ether Bond for Optical Coatings

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Solution Overview

Problem

Existing urethane compounds used in coating materials, UV-curable paints, and adhesives lack superior curability, adhesion to substrates, transparency, and molecular flexibility, particularly in applications requiring high refractive indices and optical properties.

Innovation Solution

Development of ethylenically-unsaturated-group containing reactive urethane compounds formed by reacting an unsaturated-group containing isocyanate with compounds having aliphatic, aromatic, or heterocyclic residues with hydroxyl, mercapto, or amino groups, or by reacting with polymer compounds having active hydrogen functional groups, resulting in curable compositions and cured materials with enhanced properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional isocyanate compounds are used to form urethane bonds, then basic coating and adhesive properties are achieved, but curability, adhesion strength, transparency, and molecular flexibility are insufficient

Engineering Contradiction:
ImprovecurabilityVSAvoidmolecular flexibility
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent modifies the molecular structure of isocyanate compounds by introducing ether bonds at specific positions (alpha or beta carbons relative to the isocyanate group). This structural parameter change enables the resulting urethane compounds to simultaneously achieve superior curability through enhanced reactivity and molecular flexibility through the flexible ether linkage, resolving the contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures combining isocyanate groups with ether-containing hydrocarbon chains. The ether bond serves as a flexible spacer that connects functional groups while maintaining molecular mobility. This composite approach allows the material to exhibit both high reactivity (curability) and flexibility, overcoming the limitations of conventional rigid urethane structures.

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If aromatic compounds are used to increase refractive index for optical applications, then transparency is improved, but adhesion strength and flexibility deteriorate

Engineering Contradiction:
ImprovetransparencyVSAvoidadhesion strength
Core Design Contradiction:
Illumination intensityVSStrength

Solution Approach 1:

The patent introduces aromatic groups at specific local positions within the molecular structure (e.g., as substituents on the hydrocarbon chain rather than as the main backbone). This localized incorporation of aromatic rings provides the necessary transparency and refractive index for optical applications while the rest of the molecular structure (ether linkages and aliphatic portions) maintains flexibility and adhesion properties.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The invention changes the spatial arrangement and concentration of aromatic groups within the molecule. By controlling the position and number of aromatic substituents, the patent optimizes the balance between optical properties (transparency) and mechanical properties (adhesion), allowing the material to satisfy both requirements simultaneously.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If high reactivity is achieved through functional group introduction, then curability improves, but molecular flexibility and processing ease worsen

Engineering Contradiction:
ImprovecurabilityVSAvoidprocessing ease
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The ether bond serves as an intermediary element between the isocyanate functional groups and the rest of the molecular structure. This ether linkage mediates between the high reactivity required for curability and the flexibility needed for processing, allowing the functional groups to remain highly reactive while the ether spacers provide molecular mobility and processability.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 reactive urethane compounds demonstrate improved curability, adhesion, transparency, and mechanical properties, suitable for applications in optical materials, color filters, and solder resists, with enhanced sensitivity, heat resistance, and chemical resistance.

Implementation Method 1

a method of allowing an isocyanate compound to react with various compounds having active hydrogen

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

ethylenically-unsaturated-group containing reactive urethane compounds... curable compositions containing such reactive urethane compounds and cured materials thereof

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Data Source

PatentEP2154162B1Reactive urethane compound having ether bond, curable composition and cured material
Publication Date: 2019.07.17 RESONAC HOLDINGS CORP
  • EP2154162B1 patent drawingFigure 1
  • EP2154162B1 patent drawingFigure 2
  • EP2154162B1 patent drawingFigure 3

AI summary

An object of the present invention is to provide a reactive urethane compound having superior curability, adhesion to substrates, transparency, molecular flexibility, and mechanical properties, a curable composition containing the compound, and a cured material formed from the composition. An ethylenically-unsaturated-group containing reactive urethane compound of the present invention is represented by formula (I): wherein R1 and R2 are each independently a hydrogen atom or an alkylene group; R3 is a hydrogen atom, a alkyl group, or an aryl group; R4 is a single bond or an alkylene group; R5 is a hydrogen atom or a methyl group; R6 is an oxygen atom, a sulfur atom, or an imino group; n is 2 to 12; m is 1 to 300; and X is an aliphatic, aromatic or heterocyclic compound residue.