Reactive Dyes with Composite Anchors for Dark Shade Fastness

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Solution Overview

Problem

Existing reactive dyes for dyeing hydroxyl-, amino-, and carboxamido-containing materials suffer from low fixation, moderate wet fastness, and light fastness, limiting their performance and range of shades, especially in achieving dark colors.

Innovation Solution

Development of reactive dyes with a specific formula (I) containing a reactive anchor, which allows for superior wet and light fastness, ecological profile, and the ability to produce a wide range of darker shades, including dark violets, browns, and blacks, through diazotization and coupling reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If known reactive dyes are used for dyeing hydroxyl-, amino-, and carboxamido-containing materials, then the dyeing process is simple, but the fixation is low and wet fastness is moderate

Engineering Contradiction:
ImprovefixationVSAvoiddye structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs composite dye structures combining multiple functional groups (reactive anchors, azo moieties, coupling components) within a single dye molecule. This composite approach enables simultaneous achievement of high fixation through reactive anchors and improved wet fastness through the协同 effect of multiple functional groups, resolving the contradiction between reliability and structural complexity.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent systematically varies structural parameters of the dye molecules including the type of reactive anchor (halo-triazine, s-triazine), the nature of coupling components (K1-K8 with different substituent patterns), and the configuration of azo moieties. These parameter changes enable optimization of fixation and wet fastness properties while maintaining manageable structural complexity.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If known reactive dyes are used, then the dyeing process is straightforward, but light fastness is moderate

Engineering Contradiction:
Improvelight fastnessVSAvoiddye structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent utilizes composite dye architectures where the combination of reactive anchors, azo moieties, and specifically designed coupling components (K1-K8 with electron-donating and electron-withdrawing groups) creates a synergistic effect that enhances light fastness. The multiple functional groups work together to stabilize the dye structure against photo-degradation while maintaining reasonable structural complexity.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes light fastness by varying structural parameters including the position and type of substituents on coupling components, the configuration of azo linkages, and the selection of reactive anchor types. These parameter adjustments enable enhanced light fastness without excessive increase in structural complexity.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If known dyes are used, then the color range is limited, but the dyeing process is simple

Engineering Contradiction:
Improveshade rangeVSAvoiddye structure complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent achieves extensive shade range including dark violets, browns, and blacks by systematically varying key structural parameters: the type of diazo component (B1-B4 with different aromatic structures), the configuration of azo moieties (number and position), and the substituents on coupling components (K1-K8 with different electron-donating/withdrawing groups). These parameter variations enable broad color adaptation while maintaining manageable structural complexity through modular design.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a segmented modular dye structure where the overall molecule is divided into distinct functional segments (reactive anchor, azo moieties, coupling components with specific substituents). This segmentation allows independent optimization of each segment for color properties while maintaining overall structural manageability, enabling wide shade range without excessive complexity.

Inventive Principle:
Principle #1Segmentation

4Object-affected harmful factors

If known reactive dyes are used, then ecological profile is moderate, but the dyeing process is conventional

Engineering Contradiction:
Improveecological profileVSAvoiddye structure complexity
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent improves ecological profile by optimizing structural parameters including the selection of reactive anchor types (halo-triazine and s-triazine groups that provide high fixation with reduced unfixed dye waste), the choice of coupling components with environmentally benign substituents, and the configuration of azo moieties for enhanced stability. These parameter changes reduce harmful effects while maintaining reasonable structural complexity.

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 new dyes exhibit enhanced wet and light fastness, improved ecological profile, and the capability to achieve a broader spectrum of darker shades, surpassing the limitations of previous dyes in terms of color range and durability.

Implementation Method 1

diazotization of the compounds of the formula (IV) and reacting the correspondingly obtained diazonium salts with a compound of the formula K to obtain the intermediate of general formula (V)

Methodology Applied
Scientific EffectDiazotization: Chemical Bonding

Implementation Method 2

reacting the correspondingly obtained diazonium salts with a compound of the formula K to obtain the intermediate of general formula (V)

Methodology Applied
Scientific EffectCoupling reaction: Chemical Bonding

Data Source

PatentEP2875076B1Reactive dyes, process for the production thereof and their use
Publication Date: 2018.08.15 DYSTAR COLOURS DISTRIBUTION GMBH
  • EP2875076B1 patent drawing
  • EP2875076B1 patent drawing
  • EP2875076B1 patent drawing

AI summary

The present invention relates to reactive dyes of the formula (I), in which n, A, B and K are defined as given in claim, a process for preparing them, and their use for dyeing and printing hydroxyl-, amino-, and/or carboxamido-containing materials.