Dimeric anionic monoazo dyes

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Solution Overview

Problem

Current dimeric monoazo dyes lack improved properties such as uniform color shade (levelness), light and wet/wash fastness, and build-up behavior, making them unsuitable for efficient dyeing and printing of organic substrates like paper and polyamides.

Innovation Solution

Development of a novel dimeric anionic monoazo dye with specific structural features, including SO3H groups in ortho-position to azo groups, which enhances light and wet/wash fastness and build-up behavior, suitable for dyeing and printing organic substrates through processes like inkjet printing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional dimeric monoazo dyes are used, then the dyeing process can be performed, but the dye levelness (uniformity of color shade) is insufficient

Engineering Contradiction:
Improvedye levelnessVSAvoidcolor uniformity
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent introduces specific local structural features into the dye molecule, including sulfonate groups at defined positions and particular substituent patterns on the aromatic rings. These localized structural modifications create specific interaction sites that improve uniformity of dye distribution and binding, directly addressing the color uniformity issue while maintaining the overall dimeric monoazo structure.

Inventive Principle:
Principle #3Local quality

2Reliability

If conventional dimeric monoazo dyes are used, then the dyeing process can be performed, but the light and wet/wash fastness is insufficient

Engineering Contradiction:
Improvecolor fastnessVSAvoidresistance to fading
Core Design Contradiction:
ReliabilityVSDuration of action of moving object

Solution Approach 1:

The patent creates a composite molecular structure by combining multiple aromatic rings with specific substituent patterns, sulfonate groups, and azo linkages in a dimeric arrangement. This composite structure provides multiple interaction points with the substrate and enhanced molecular stability, resulting in improved resistance to light, washing, and rubbing while maintaining the essential monoazo character.

Inventive Principle:
Principle #40Composite materials

3Productivity

If conventional dimeric monoazo dyes are used, then the dyeing process can be performed, but the build-up behavior is insufficient

Engineering Contradiction:
Improvebuild-up behaviorVSAvoiddye uptake efficiency
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent modifies key structural parameters of the dye molecule, including the position and nature of substituents on the aromatic rings, the placement of sulfonate groups, and the overall molecular geometry. These parameter changes optimize the dye's affinity for the substrate and its ability to build up color intensity efficiently, improving productivity without requiring excessive dye quantities.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2910608B1Dimeric anionic monoazo dyes
Publication Date: 2017.05.31 ARCHROMA IP GMBH
  • EP2910608B1 patent drawing
  • EP2910608B1 patent drawing
  • EP2910608B1 patent drawing

AI summary

A compound of the general formula (I), a process for its manufacture and its use for dyeing and/or printing organic substrates.