Oxetane-Based Cationic Ink Resists Oxygen Inhibition

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Solution Overview

Problem

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

Innovation Solution

A curable composition incorporating a monomer composition with 3-allyloxyoxetane or 3-(2-ethylhexyloxy)oxetane as cationically curable monomers, along with an epoxy compound and a photoacid generator, which allows for rapid curing under UV irradiation even in the presence of oxygen and water, with excellent substrate adhesion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If vinyl ether compound having a cyclic ether skeleton is used in large amount to improve substrate adhesion and curability, then substrate adhesion is improved, but the composition absorbs moisture and becomes susceptible to cure inhibition by water

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

Solution Approach 1:

The patent changes the chemical structure parameter of the cyclic ether compound from vinyl ether to oxetane type, which fundamentally alters the moisture interaction properties while maintaining the cyclic ether skeleton. This structural parameter change allows the compound to provide good substrate adhesion without the moisture absorption problem that plagues vinyl ether compounds.

Inventive Principle:
Principle #35Parameter changes

2Ease of operation

If low-viscosity ink is used to improve dischargeability, then dischargeability is improved, but oxygen diffusion into the ink is facilitated causing cure inhibition

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

Solution Approach 1:

The patent converts the harmful effect of oxygen into a beneficial outcome by using a cationic curing mechanism that is inherently resistant to oxygen inhibition. The oxetane-based monomers undergo cationic polymerization that proceeds even in the presence of oxygen, transforming what was previously a harmful factor (oxygen diffusion in low-viscosity inks) into a non-issue, allowing the ink to maintain low viscosity for good dischargeability without suffering from cure inhibition.

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

3Productivity

If radically-curable ink is used to achieve rapid curability, then curability speed is improved, but substrate adhesion deteriorates and oxygen inhibition occurs

Engineering Contradiction:
Improvecuring speedVSAvoidsubstrate adhesion
Core Design Contradiction:
ProductivityVSStrength

Solution Approach 1:

The patent inverts the conventional approach by using cationic curing instead of radical curing. While radical curing is the conventional fast method, it suffers from adhesion and oxygen inhibition problems. The invention reverses the paradigm by employing cationic polymerization with oxetane monomers, which provides both rapid curability and excellent substrate adhesion, effectively turning the disadvantages of radical curing into advantages through this inversion of the curing mechanism.

Inventive Principle:
Principle #13The other way round (Inversion)

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 composition achieves rapid curing and excellent substrate adhesion, resisting moisture absorption and reducing unreacted monomers, thus providing stable and odor-free UV-curable inkjet inks with high definition printing capabilities.

Implementation Method 1

The curable composition can be rapidly cured by ultraviolet irradiation

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP3162835B1Monomer composition and curable composition containing same
Publication Date: 2019.12.11 DAICEL CORP
  • EP3162835B1 patent drawing
  • EP3162835B1 patent drawing
  • EP3162835B1 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 at least one cationically curable monomer. The at least one cationically curable monomer includes at least one of 3-allyloxyoxetane and 3-(2-ethylhexyloxy)oxetane. The at least one of 3-allyloxyoxetane and 3-(2-ethylhexyloxy)oxetane is present in a total content of 5 weight percent or more of the total weight of the monomer composition.