Vinyl Ether Monomer Composition for Oxygen-Resistant Curing

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Solution Overview

Problem

Cationically-curable inks containing vinyl ether compounds with a cyclic ether skeleton are unsuitable due to moisture absorption, leading to cure inhibition and curing failure in high-humidity conditions, while radically-curable inks suffer from oxygen inhibition and poor substrate adhesion.

Innovation Solution

A monomer composition comprising a hydroxy-free multifunctional vinyl ether compound and a hydroxy-containing vinyl ether compound, combined with a photoacid generator, which allows for rapid curing even in the presence of oxygen and water, and forms a cured product with excellent adhesion to various substrates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If vinyl ether compounds with cyclic ether skeleton are used in cationically-curable inks, then substrate adhesion is improved, but moisture absorption increases leading to cure inhibition and curing failure in high-humidity conditions

Engineering Contradiction:
Improvesubstrate adhesionVSAvoidcure reliability in humid conditions
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The invention changes the chemical composition parameters by specifying that vinyl ether compounds with cyclic ether skeleton must be less than 30 wt% of total monomers, while hydroxy-containing vinyl ether compounds must be 5-30 wt%. This parameter adjustment reduces moisture absorption while maintaining adhesion through the hydroxy-containing component.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite monomer system combining multiple vinyl ether compound types (hydroxy-containing and non-hydroxy-containing) with specific proportions. This composite approach balances the adhesion benefits of cyclic ether structures with the moisture resistance of hydroxy-containing compounds.

Inventive Principle:
Principle #40Composite materials

2Speed

If radically-curable inks are used, then rapid curability is achieved, but oxygen inhibition causes cure inhibition and poor substrate adhesion

Engineering Contradiction:
Improvecurability speedVSAvoidsubstrate adhesion
Core Design Contradiction:
SpeedVSStrength

Solution Approach 1:

The invention substitutes radical-based curing mechanism with cationic curing mechanism. This replacement eliminates oxygen inhibition (a chemical interference) while maintaining rapid curability through photoacid generator-mediated cationic polymerization of vinyl ether compounds.

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

Solution Approach 2:

The invention changes the curing mechanism parameter from radical to cationic, and adjusts monomer composition to use vinyl ether compounds (5-80 wt%) instead of traditional radical monomers. This achieves both rapid curing and superior substrate adhesion without oxygen inhibition.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If low-viscosity inks are used for good dischargeability, then oxygen diffusion into the ink increases, leading to increased cure inhibition

Engineering Contradiction:
ImprovedischargeabilityVSAvoidoxygen diffusion and cure inhibition
Core Design Contradiction:
Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The invention converts the harmful effect of oxygen diffusion into a non-issue by using cationic curing mechanism that is inherently resistant to oxygen inhibition. The low-viscosity formulation (achieved through monomer selection) maintains good dischargeability while the cationic mechanism eliminates the harmful interaction with oxygen.

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

4Strength

If vinyl ether compounds with cyclic ether skeleton are used to improve adhesion, then moisture absorption increases causing cure inhibition by water

Engineering Contradiction:
Improvesubstrate adhesionVSAvoidmoisture absorption and water inhibition
Core Design Contradiction:
StrengthVSObject-affected harmful factors

Solution Approach 1:

The invention changes the monomer composition parameters by limiting cyclic ether skeleton compounds to less than 30 wt% and introducing hydroxy-containing vinyl ether compounds (5-30 wt%). This parameter change reduces overall moisture absorption while maintaining adhesion through hydrogen bonding capability of hydroxy groups.

Inventive Principle:
Principle #35Parameter changes

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 curable composition exhibits rapid curing, low viscosity, and excellent substrate adhesion, maintaining stability even in humid conditions, reducing unreacted monomers and odor generation, making it suitable for UV-curable inkjet inks.

Implementation Method 1

the monomer composition, when incorporated with a photoacid generator, gives a curable composition that has excellent curing sensitivity and, upon ultraviolet irradiation, can be rapidly cured

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP3162822B1Monomer composition and curable composition containing same
Publication Date: 2020.08.26 DAICEL CORP
  • EP3162822B1 patent drawing
  • EP3162822B1 patent drawing
  • EP3162822B1 patent drawing

AI summary

Provided is a monomer composition that has rapid curability and can be rapidly cured even in the presence of oxygen and/or water, to form a cured product having excellent adhesion to a wide variety of substrates. The monomer composition according to the present invention includes vinyl ether compounds (A). The monomer composition contains a monofunctional monomer in an amount of 20 to 80 weight percent, a hydroxy-free multifunctional vinyl ether compound in an amount of 5 to 80 weight percent, and a hydroxy-containing vinyl ether compound in an amount of 0.1 weight percent to less than 10 weight percent, where all weight percentages are based on the total weight of the monomer composition.