Disperse Azo Dye Structure for Washing and Sublimation Fastness

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Solution Overview

Problem

Existing disperse azo dyes do not achieve optimal fastness to washing and sublimation, which is crucial for dyeing hydrophobic materials like polyesters and blended fibers.

Innovation Solution

Development of disperse azo dyes with specific ester groups linked to the chromophore via a linker, specifically diazotized and coupled using known methods, resulting in dyes with improved fastness properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional disperse azo dyes are used, then the dyeing process is simple, but the washing fastness and sublimation fastness are insufficient

Engineering Contradiction:
Improvewashing fastness and sublimation fastnessVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The dye molecule is segmented into distinct functional modules: a chromophore unit (azo group), a linker unit (containing ester groups at specific positions), and a diazo component. This segmentation allows optimization of each module's function - the chromophore provides color, the linker ensures fastness properties, and the diazo component enables dyeing - while maintaining overall molecular stability and performance

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention creates a composite molecular structure combining multiple functional groups (azo chromophore, ester linkers, diazo components) into a single integrated dye molecule. This composite structure synergistically provides both the desired color properties and enhanced washing/fastness properties that individual components cannot achieve alone

Inventive Principle:
Principle #40Composite materials

2Reliability

If ester groups are linked directly to the chromophore, then the structure is simple, but the fastness properties are not optimized

Engineering Contradiction:
Improvefastness to washing and sublimationVSAvoidlinker structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

A linker unit containing ester groups at the ortho position to the azo bridge is introduced as an intermediary between the chromophore and the diazo component. This intermediary structure mediates the interaction between the chromophore and the fiber, enhancing fastness properties by providing optimal spacing, orientation, and chemical interaction capabilities while maintaining structural stability

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention optimizes specific molecular parameters including the position of ester groups (ortho position to azo bridge), the type of substituents (R1-R7 groups), and the linker structure (L group) to achieve optimal fastness properties. By systematically varying these parameters, the dye molecules achieve enhanced washing and sublimation fastness while maintaining color properties

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 dyes exhibit excellent washing fastness and very good sublimation fastness, ensuring even color tones and high durability on hydrophobic materials such as polyesters and blended fibers.

Implementation Method 1

a compound of the general formula (III) D-NH2 (III) where D is defined as stated above is diazotized and converted to a compound of the general formula (IV)

Methodology Applied
Scientific EffectDiazotization: Chemical Bonding

Implementation Method 2

The coupling of the diazotized compounds to the compounds of the general formula (IV) is generally also carried out in a known manner

Methodology Applied
Scientific EffectAzo coupling: Chemical Bonding

Data Source

PatentEP2125962B1Dispersion dye, the production and use thereof
Publication Date: 2013.05.22 DYSTAR COLOURS DEUTSCHLAND GMBH
  • EP2125962B1 patent drawing
  • EP2125962B1 patent drawing
  • EP2125962B1 patent drawing

AI summary

The present invention relates to a dye of the general formula (I), wherein D signifies the residue of a diazo component; R1 bis R7 and L are defined as disclosed in claim 1, a method for the production thereof, and the use thereof.