Water-Soluble Disazo Compound Ink for High Vividness and Fastness

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Solution Overview

Problem

Conventional yellow inkjet inks, such as C.I. Direct Yellow 132, fail to meet requirements for hue, vividness, light fastness, moisture fastness, ozone gas fastness, and storage stability, leading to issues like nozzle clogging and insufficient color density.

Innovation Solution

A water-soluble disazo compound with specific structural formulas is developed, which forms the basis of an ink composition that maintains high solubility, prevents crystal precipitation, and ensures stable storage and high color density, suitable for inkjet recording on various materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional water-soluble dyes (e.g., C.I. Direct Yellow 132) are used in inkjet inks, then water-solubility is improved, but crystal precipitation occurs when water evaporates near the nozzle, leading to nozzle clogging

Engineering Contradiction:
Improvewater-solubilityVSAvoidnozzle clogging
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters of the dye molecule by introducing specific substituents (sulfonate groups, hydroxyl groups, and aromatic hydrocarbon groups) to achieve optimal solubility and prevent precipitation. The general formula (1) shows multiple positions for hydrophilic substituents that can be adjusted to balance solubility and precipitation resistance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining hydrophilic portions (sulfonate groups, hydroxyl groups) with hydrophobic portions (aromatic hydrocarbon groups). This composite structure allows the dye to maintain water solubility while preventing crystal precipitation through the balanced molecular architecture.

Inventive Principle:
Principle #40Composite materials

2Illumination intensity

If conventional yellow dyes are used to achieve sufficient color density, then hue and vividness are improved, but light fastness and ozone gas fastness deteriorate

Engineering Contradiction:
Improvecolor density and vividnessVSAvoidlight fastness and gas fastness
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The invention modifies the chemical structure parameters by introducing specific substituents at defined positions in the azo compound molecule. The sulfonate groups at positions R1-R6 and hydroxyl groups at R7-R12, along with aromatic hydrocarbon groups, are carefully positioned to enhance both color properties and fastness without compromising solubility.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the potential harm of strong chromophoric groups (which provide vivid color but poor fastness) into benefit by strategically positioning them within a protected molecular framework. The specific substitution pattern creates a structure where the chromophore is shielded by surrounding groups, maintaining vividness while improving resistance to light and ozone degradation.

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

3Illumination intensity

If the concentration of coloring matter is increased to achieve high color density, then hue vividness is improved, but storage stability deteriorates due to increased precipitation risk

Engineering Contradiction:
Improvecolor densityVSAvoidstorage stability
Core Design Contradiction:
Illumination intensityVSStability of the object's composition

Solution Approach 1:

The invention optimizes the molecular parameters by incorporating multiple hydrophilic groups (sulfonate and hydroxyl) that enhance water solubility, allowing high concentrations of coloring matter to be maintained in solution without precipitation. The general formula (1) provides multiple substitution positions that can be adjusted to achieve the desired concentration and color density while maintaining storage stability.

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 ink composition provides excellent water fastness, moisture fastness, gas fastness, particularly light fastness, and long-term storage stability, with vivid yellow hue and high color density, effectively addressing the limitations of existing inks.

Implementation Method 1

a water-soluble disazo compound... which maintains high solubility, prevents crystal precipitation

Methodology Applied
Scientific EffectSolubility: Solvation

Implementation Method 2

to dry quickly on a record-receiving material

Methodology Applied
Scientific EffectEvaporation: Evaporation

Data Source

PatentEP2096145B1Water-soluble azo compounds or salts thereof, ink compositions and colored products
Publication Date: 2011.08.03 NIPPON KAYAKU CO LTD
  • EP2096145B1 patent drawing
  • EP2096145B1 patent drawing
  • EP2096145B1 patent drawing

AI summary

The present invention relates to a water-soluble azo compound or a salt thereof represented by the following formula (1): (wherein, R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a sulfo group, n, m, x and y represent an integer of 1 or 2, 1 to 3, 2 to 4 and 1 to 3, respectively.) and an ink composition containing the same; the above compound or a salt thereof has a hue possessing a high vividness suitable for inkjet recording, provides various fastnesses to recorded matters, and is useful as a yellow coloring matter excellent in storage stability when prepared into an ink composition, and suitable for ink compositions, especially inks for inkjet recording.