Azo Iron Complex Dye for Soluble, Heat-Resistant Black Ink

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing ink compositions for continuous-type ink-jet printers lack a black colorant that is free from harmful heavy metals, exhibits high solubility in organic solvents, and provides excellent heat and light resistance, while also ensuring good adhesion on non-absorbent surfaces.

Innovation Solution

Development of an azo iron complex dye with a disazo-monoazo iron complex structure, represented by specific chemical formulas, which includes electron-withdrawing groups and monovalent cations, ensuring high solubility and deep black color without heavy metals, and an ink composition containing this dye.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a black pigment is used as a colorant, then heat and light resistance is improved, but color developability deteriorates and aggregation occurs resulting in poor storage stability

Engineering Contradiction:
Improveheat and light resistanceVSAvoidcolor developability
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The invention changes the chemical parameters by using a disazo-monoazo iron complex structure with specific substituent groups (electron-withdrawing groups at para-position of azo group, alkyl groups with specific carbon numbers) to achieve both black color and high solubility. This parameter optimization allows the dye to maintain heat and light resistance while improving color developability and storage stability through enhanced solubility in organic solvents.

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If a black dye is used as a colorant, then solubility in organic solvent and storage stability are improved, but heat and light resistance deteriorates

Engineering Contradiction:
Improvestorage stabilityVSAvoidheat and light resistance
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The invention creates a composite structure by forming an iron complex with a specific disazo-monoazo dye molecule. This composite structure combines the solubility advantages of dye molecules with the heat and light resistance properties of metal complexes. The iron complexation with the disazo-monoazo ligand system provides both good solubility in organic solvents and excellent heat and light resistance, resolving the contradiction between storage stability and reliability.

Inventive Principle:
Principle #40Composite materials

3Stability of the object's composition

If an azo chromium complex dye is used as a black colorant, then solubility in organic solvent and heat resistance are improved, but environmental safety deteriorates due to toxic heavy metal chromium

Engineering Contradiction:
Improvesolubility in organic solventVSAvoidenvironmental safety
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The invention extracts and removes the harmful chromium metal from the complex dye structure while retaining the beneficial disazo-monoazo ligand system. By replacing chromium with iron (a less toxic metal) and optimizing the organic ligand structure with specific electron-withdrawing groups and alkyl chains, the invention maintains high solubility in organic solvents and heat resistance while eliminating environmental toxicity. This extraction of the harmful element while preserving functional structure resolves the contradiction between solubility and environmental safety.

Inventive Principle:
Principle #2Taking out (Extraction)

4Object-affected harmful factors

If existing iron complex dyes are used, then environmental safety is improved by avoiding chromium, but color quality deteriorates as they appear brown or reddish brown rather than true black

Engineering Contradiction:
Improveenvironmental safetyVSAvoidcolor quality
Core Design Contradiction:
Object-affected harmful factorsVSManufacturing precision

Solution Approach 1:

The invention applies local quality optimization by introducing specific electron-withdrawing groups (such as nitro, cyano, or carbonyl groups) at the para-position of the azo group and specific alkyl groups with defined carbon numbers at other positions. These localized structural modifications to the disazo-monoazo ligand system tune the electronic distribution and light absorption properties, achieving true black color while maintaining environmental safety through iron complexation. The specific local structural features enable precise control over color quality without compromising environmental benefits.

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS12384920B2Azo iron complex dye, ink composition containing same, and method for producing azo iron complex dye
Publication Date: 2025.08.12 ORIENT CHEM INDS
  • US12384920B2 patent drawing
  • US12384920B2 patent drawing
  • US12384920B2 patent drawing

AI summary

An azo iron complex dye which does not contain harmful heavy metals, exhibits sufficient solubility in organic solvents for practical use, and exhibits an excellent black color. The azo iron complex dye contains a disazo-monoazo iron complex represented by the following chemical formula (1)(in the chemical formula (1), R1 and R2 are each independently a straight or branched alkyl group having 3-10 carbon atoms, R3 is an electron-withdrawing group, R4 is a straight or branched alkyl group having 1-5 carbon atoms or a straight or branched alkoxy group having 1-5 carbon atoms, R5 is a nitro group, a sulfonamide group or a halogen atom, R6 is a hydrogen atom, a straight or branched alkyl group having 1-8 carbon atoms, a nitro group or a halogen atom, R7 is a hydrogen atom or a straight or branched alkyl group having 3-12 carbon atoms, and A+ is a monovalent cation).