Azo Compound Ink Composition Ozone Resistance

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Solution Overview

Problem

Current inkjet recording technologies face challenges in achieving superior ozone gas resistance, bronzing resistance, and color-rendering properties, particularly for black ink compositions, which often result in poor print quality and stability issues.

Innovation Solution

An azo compound with a specific skeleton is developed, which forms the basis of an ink composition that exhibits excellent ozone gas resistance, high print density, and superior bronzing resistance, ensuring high-quality black ink performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional water-soluble coloring matters are used in inkjet recording, then the ink composition can be prepared easily with good solubility, but the recorded images show poor gas resistance (discoloration and fading due to ozone gas)

Engineering Contradiction:
Improveease of ink composition preparationVSAvoidgas resistance of recorded images
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the coloring matter from conventional water-soluble dyes to a specifically designed azo compound with formula (1). This structural parameter change introduces a sulfonate group and specific substituents (R1-R15) that enhance ozone resistance while maintaining water solubility through the sulfonate functionality, thus resolving the contradiction between ease of preparation and gas resistance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining an azo chromophore with electron-donating substituents and a sulfonate anchoring group. This composite structure integrates the color-generating capability of the azo group with the stability-providing electron-donating groups and the solubility-providing sulfonate group, achieving simultaneous improvement in gas resistance, solubility, and ease of ink formulation.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If metal phthalocyanine-based dyes are used to achieve high print density, then the coloring matter provides strong color intensity, but a bronzing phenomenon occurs causing poor print quality and off-balanced images

Engineering Contradiction:
Improveprint density and image qualityVSAvoidbronzing phenomenon
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and eliminates the problematic metal ion component from metal phthalocyanine dyes while retaining the beneficial azo chromophore structure. By removing the metal center that causes bronzing, the invention achieves high print density through the extended conjugation of the azo groups without the harmful metallic sheen and color distortion associated with metal-containing dyes.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces expensive and problematic metal-containing dyes with a organic azo compound that, while simpler in composition, provides comparable or superior performance. The organic structure avoids the bronzing issue entirely and allows for easier formulation and handling, effectively substituting a problematic material with a superior alternative.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Adaptability or versatility

If oxidizing gases (ozone, NOx, SOx) are present in the environment, then atmospheric conditions are normal, but the recorded images undergo discoloration and fading

Engineering Contradiction:
Improvecompatibility with environmental conditionsVSAvoiddiscoloration and fading of recorded images
Core Design Contradiction:
Adaptability or versatilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies preliminary anti-action by incorporating electron-donating substituents (R1-R15) into the azo compound structure before exposure to environmental conditions. These substituents pre-establish a protective electronic environment around the chromophore, creating repulsion or stabilization against oxidizing attacks from ozone and other atmospheric oxidants, thus preventing discoloration before it can occur.

Inventive Principle:
Principle #9Preliminary anti-action

Solution Approach 2:

The molecular structure of the azo compound creates an electronically inert environment around the chromophore through the electron-donating substituents. This internal protective shell effectively isolates the color-generating azo group from external oxidizing agents, mimicking the effect of an inert atmosphere and preventing chemical reactions that would lead to fading and discoloration.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

4Quantity of substance

If conventional coloring matters are used to achieve satisfactory solubility in water, then the ink can be formulated as aqueous solution, but the storage stability and image fastness properties are insufficient

Engineering Contradiction:
Improvesolubility in waterVSAvoidstorage stability and image fastness
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent applies local quality by differentiating the functional roles of different parts of the molecule: the azo chromophore core provides color and stability, the electron-donating substituents (R1-R15) provide environmental resistance and structural stability, while the sulfonate group provides localized water solubility. This spatial differentiation of functions allows each part to optimize its specific role without compromising the others, achieving simultaneous improvement in solubility and stability.

Inventive Principle:
Principle #3Local quality

Data Source

PatentEP3354692B1Azo compound, ink composition, ink jet recording method, and colored article
Publication Date: 2021.04.14 NIPPON KAYAKU CO LTD
  • EP3354692B1 patent drawing
  • EP3354692B1 patent drawing
  • EP3354692B1 patent drawing

AI summary

This azo compound and an ink composition containing same are used suitably as inks for ink jet recording and have especially excellent gas (ozone) resistance when recording is done on special ink jet paper. An azo compound represented by formula (1) or a tautomer thereof, or a salt of these. [In formula (1), R1 represents a C1-C4 alkyl group or the like, R2 represents a cyano group or the like, R3 and R4 each independently represent a C1-C4 alkoxy group or the like, R5-R10 each independently represent a group represented by formula (2) or the like, and R11-R13 each independently represent a nitro group or the like. In formula (2), R14 is an anilino group or the like, and R15 is a mono- or di-C1-C6 alkylamino group or the like.]