Acid Azo Dye Composition for Polyamide Fastness and Exhaustion

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Solution Overview

Problem

Existing acid dyes lack improved properties for effective dyeing of organic substrates, particularly in terms of fastness and compatibility with natural and synthetic polyamides.

Innovation Solution

Development of novel acid dyes with specific chemical structures, such as compounds of formula (I), which include anionic substituents and specific alkyl or aryl groups, allowing for improved dyeing properties and compatibility with polyamides, and a process for their preparation involving diazotization and coupling reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional acid dyes are used, then the dyeing process is simple, but the fastness level and exhaustion rate are insufficient

Engineering Contradiction:
Improvefastness levelVSAvoidchemical structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of acid dyes through specific substituents (anionic groups like carboxyl and sulpho, aromatic hydrocarbon radicals with 6-20 carbon atoms) to achieve improved fastness levels and exhaustion rates while maintaining practical dyeing applications

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If existing acid dyes are used, then the process is conventional and simple, but the compatibility with natural and synthetic polyamides is insufficient

Engineering Contradiction:
Improvecompatibility with polyamidesVSAvoidmanufacturing complexity
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent applies local quality by introducing specific functional groups (anionic substituents) at particular positions on the dye molecule to enhance compatibility with polyamide substrates, while the core structure remains suitable for conventional dyeing processes

Inventive Principle:
Principle #3Local quality

3Reliability

If novel acid dyes with specific structures are developed, then fastness and exhaustion rates improve, but the synthesis process becomes more complex

Engineering Contradiction:
Improvefastness levelVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the dye molecule into distinct functional components (anionic substituents, aromatic hydrocarbon radicals, coupling components) that can be systematically combined through conventional diazotization and coupling reactions to achieve improved performance

Inventive Principle:
Principle #1Segmentation

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 acid dyes provide high fastness levels, excellent exhaustion rates, and consistent hue on polyamide substrates, suitable for various dyeing processes including Inkjet printing, with good light and wet fastness properties.

Implementation Method 1

both the amine functions or the amine function of compounds of the formula (II) which are known from the literature are conventionally diazotized by adding nitrosylsulphuric acid or sodium nitrite

Methodology Applied
Scientific EffectDiazotization: Chemical Bonding

Implementation Method 2

the diazotized or bis-diazotized diamine is allowed to react with the compound (III), preferably in aqueous solution

Methodology Applied
Scientific EffectCoupling reaction: Chemical Bonding

Data Source

PatentEP2251387B1Acidic azo dyes
Publication Date: 2012.02.29 CLARIANT FIANCE (BVI) LTD
  • EP2251387B1 patent drawing
  • EP2251387B1 patent drawing
  • EP2251387B1 patent drawing

AI summary

Acid dyes, a process for their preparation and their use for dyeing organic substrates of the general formula (I) wherein the substituents have the meaning as indicated in the claims.