Azo Dye Purification Using Urea Complexation

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Solution Overview

Problem

Azo dye compounds with high crystallinity are difficult to dissolve in solvents, making it challenging to obtain high purity through purification methods like recrystallization.

Innovation Solution

An azo dye composition comprising an azo dye compound represented by Formula (I) and a urea compound represented by Formula (II), where at least one of R11, R12, R13, or R14 is a halogen atom, and R21 and R22 are aliphatic groups, is used, with a method involving precipitation using a first solvent and a second solvent different from the urea compound, to reduce impurities and achieve high purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If an azo dye compound with high crystallinity is used, then the dye has good stability and color fastness, but it becomes difficult to dissolve in solvents and hard to purify by recrystallization

Engineering Contradiction:
ImprovestabilityVSAvoidsolubility
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

A urea compound is introduced as an intermediary substance to facilitate the dissolution of the azo dye compound. The urea compound forms a complex with the azo dye, increasing its solubility in the solvent and enabling effective purification through recrystallization while maintaining the dye's stability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The solubility parameters of the azo dye compound are changed by forming a complex with the urea compound. This chemical interaction modifies the physical properties of the dye, particularly its solubility characteristics, allowing it to dissolve in solvents where it would otherwise be insoluble due to high crystallinity

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If an azo dye compound with high crystallinity is used, then the dye has good stability, but it becomes difficult to obtain high purity by purification

Engineering Contradiction:
ImprovestabilityVSAvoidpurity
Core Design Contradiction:
Stability of the object's compositionVSManufacturing precision

Solution Approach 1:

The urea compound acts as a mediating agent during the purification process. It forms a soluble complex with the azo dye compound, allowing impurities to be separated through filtration or decantation. The complex can then be decomposed to yield high-purity dye, thus achieving both stability and purity

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The urea compound is added before the purification step to pre-modify the azo dye compound's solubility characteristics. This preliminary action enables subsequent purification operations to be effective, transforming an otherwise unpurifiable high-crystallinity dye into a purifiable form

Inventive Principle:
Principle #10Preliminary action

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 method results in an azo dye compound of high purity, with a reduced amount of impurities, as the interaction between the azo dye compound and urea compound facilitates solubility and purification, allowing for the isolation of a high-purity azo dye compound.

Implementation Method 1

an azo dye composition including an azo dye compound and a urea compound... the azo dye composition includes an azo dye compound and a urea compound

Methodology Applied
Scientific EffectComplex formation:

Implementation Method 2

precipitating the azo dye composition by bringing the crude product into contact with a first solvent in a second solvent

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Data Source

PatentEP3190158B8Azo dye composition and method for producing same
Publication Date: 2018.12.26 FUJIFILM CORP

AI summary

Provided are an azo dye composition including an azo dye compound represented by Formula (I) and a urea compound represented by Formula (II), and a method for producing an azo dye composition. R11, R12, R13 and R14 each independently represent a hydrogen atom, a halogen atom, or an aliphatic group; R15 represents an aliphatic group; R21 and R22 each independently represent a hydrogen atom, an aliphatic group, or an aromatic group; and n represents an integer from 0 to 2.