Trisazo acid dyes

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Solution Overview

Problem

There is a need for trisazo acid dyes with improved properties such as dye levelness, color fastness, and build-up behavior, particularly for blue dyes that can be used in trichromatic printing or dyeing processes, as existing dyes face issues with uniformity, light and wet/wash fastness, and compatibility with substrates like polyamide fibers.

Innovation Solution

A novel trisazo acid dye compound of formula (I) with specific structural features, including SO3Y groups, is developed, which can be used in dyeing and printing processes, particularly for polyamide fibers, and is prepared through diazotization and coupling reactions, allowing for improved fastness and uniformity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional trisazo acid dyes are used, then basic dyeing function is achieved, but dye levelness and color fastness are insufficient

Engineering Contradiction:
Improvecolor fastnessVSAvoiddye levelness
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent modifies the molecular structure of trisazo acid dyes by introducing specific substituent groups (R1-R9) at defined positions on the aromatic rings. This structural parameter change optimizes the dye's interaction with polyamide fibers, simultaneously improving both dye levelness (uniformity of color distribution) and color fastness (resistance to fading and running), resolving the contradiction between these two properties.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If existing blue trisazo dyes are used, then blue coloration is achieved, but compatibility with trichromatic printing processes is limited

Engineering Contradiction:
Improvecompatibility with trichromatic processesVSAvoidbuild-up behavior
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent introduces specific functional groups at localized positions (R1-R9) on the dye molecule to enhance compatibility with trichromatic printing processes. These localized structural modifications improve the dye's build-up behavior (gradual color development) without compromising its blue coloration properties, enabling better adaptability to multi-color printing systems.

Inventive Principle:
Principle #3Local quality

3Reliability

If standard trisazo dyes are used, then general dyeing capability is achieved, but fastness to light and wet/wash conditions is insufficient

Engineering Contradiction:
Improvefastness to light and wet conditionsVSAvoiddye synthesis complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent incorporates photostable and wash-fast functional groups (such as sulfonate groups SO3Y) into the dye structure during the synthesis stage. This preliminary incorporation of protective functional groups ensures high fastness to light and wet/wash conditions from the outset, while the systematic synthesis approach (diazotization and coupling reactions) maintains reasonable manufacturing feasibility.

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 novel dye provides high fastness to light, wet conditions, and excellent build-up behavior, resulting in homogeneous and high-quality dyeings on polyamide fibers with good exhaustion rates and compatibility with other dyes, suitable for trichromatic processes.

Implementation Method 1

a compound of formula (II) being diazotized and coupled onto one equivalent of a compound of formula (III), the resulting amine of formula (IV) being diazotized and coupled onto one equivalent of a compound of formula (V) and the resulting amine of formula (VI) being diazotized and coupled onto one equivalent of a compound of formula (VII)

Methodology Applied
Scientific EffectDiazotization: Chemical Bonding

Implementation Method 2

a compound of formula (II) being diazotized and coupled onto one equivalent of a compound of formula (III), the resulting amine of formula (IV) being diazotized and coupled onto one equivalent of a compound of formula (V) and the resulting amine of formula (VI) being diazotized and coupled onto one equivalent of a compound of formula (VII)

Methodology Applied
Scientific EffectAzo coupling: Chemical Bonding

Data Source

PatentEP3271424B1Trisazo acid dyes
Publication Date: 2023.06.07 ARCHROMA IP GMBH
  • EP3271424B1 patent drawing
  • EP3271424B1 patent drawing
  • EP3271424B1 patent drawing

AI summary

Trisazo acid dyes of formula (I)