Acid Dye Composition for Polyamide Fastness and Level Dyeing

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Solution Overview

Problem

There is a need for acid dyes with improved properties, particularly those that can effectively dye organic substrates with enhanced fastness and compatibility, especially for natural and synthetic polyamides, while offering good light and wet fastness properties.

Innovation Solution

Development of novel acid dyes with specific chemical structures, characterized by the presence of anionic substituents and specific alkyl, alkoxy, and aryl groups, which are synthesized through conventional diazotization and coupling processes, allowing for effective dyeing of polyamides and other fibrous materials, including those used in Inkjet printing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional acid dyes are used for dyeing polyamides, then basic dyeing functionality is achieved, but light fastness and wet fastness properties are insufficient

Engineering Contradiction:
Improvelight and wet fastnessVSAvoiddye structure complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies composite material principles by creating a complex molecular structure that integrates multiple functional groups (azo chromophores, pyridone bridges, anionic substituents) into a single dye molecule. This composite structure combines the dyeing functionality with enhanced fastness properties, resolving the contradiction between basic dyeing capability and improved light/wet fastness.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent employs parameter changes by modifying the chemical structure parameters of conventional acid dyes - specifically introducing bridging members with pyridone groups and multiple anionic substituents. These structural parameter changes transform the dye's properties to achieve superior light and wet fastness while maintaining dyeing effectiveness on polyamides.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If dyes with enhanced fastness properties are developed, then dyeing quality improves, but compatibility with other dyes for combination dyeing may be reduced

Engineering Contradiction:
Improvedyeing quality and fastnessVSAvoidcompatibility for combination dyeing
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies homogeneity principles by ensuring that the novel acid dyes share common structural features (azo chromophores, anionic substituents, polyamide affinity) with conventional acid dyes. This structural homogeneity enables compatibility with other dyes in combination dyeing applications, allowing the enhanced fastness dyes to be integrated into existing dyeing systems without compromising versatility.

Inventive Principle:
Principle #33Homogeneity

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 exhaustion rates, excellent fastness properties, including light and wet fastness, and are suitable for producing level dyeings on various substrates, including wool, silk, and synthetic polyamides, with compatibility for use in combination with other dyes, enabling high-quality, consistent color outcomes.

Implementation Method 1

both the amine functions of compounds of the formula (II) which are known from the literature are conventionally diazotized and coupled onto totally two equivalents of a compound of the formula (III)

Methodology Applied
Scientific EffectDiazotization: Chemical Bonding

Implementation Method 2

both the amine functions of compounds of the formula (II) which are known from the literature are conventionally diazotized and coupled onto totally two equivalents of a compound of the formula (III)

Methodology Applied
Scientific EffectCoupling reaction: Chemical Bonding

Implementation Method 3

The dyes of the formula (I) can be isolated from the reaction medium by conventional processes, for example by salting out with an alkali metal salt, filtering and drying

Methodology Applied
Scientific EffectSalting out: Precipitation

Implementation Method 4

If desired, the dyes can be further purified by diafiltration, in which case unwanted salts and synthesis by-products are separated from the crude anionic dye

Methodology Applied
Scientific EffectDiafiltration: Semipermeable Membrane

Data Source

PatentEP2307510B1Acid dyes
Publication Date: 2012.02.29 CLARIANT FIANCE (BVI) LTD
  • EP2307510B1 patent drawing
  • EP2307510B1 patent drawing
  • EP2307510B1 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.