Phthalimido Disperse Azo Dyes for Fast Blue Textile Dyeing

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Solution Overview

Problem

Current disperse azo dyes used for hydrophobic textile materials do not consistently meet requirements for light fastness, washing fastness, and perspiration resistance, particularly in blue shades.

Innovation Solution

Development of disperse dyes with a phthalimido-substituted aniline coupling component, specifically designed to enhance fastness properties through a diazo component and coupling process, suitable for both exhaust and thermosol processes, and applicable in discharge printing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional disperse azo dyes are used for hydrophobic textile materials, then the dyeing process is simple and cost-effective, but the fastness properties to light, washing, and perspiration are insufficient

Engineering Contradiction:
Improvefastness to light, washing and perspirationVSAvoiddye molecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by modifying the molecular structure parameters of disperse azo dyes. Specifically, it introduces phthalimido-substituted aniline coupling components with controlled alkyl chain lengths (C1-C12) and substituent positions, which systematically alters the dye's chemical properties to achieve superior fastness to light, washing, and perspiration while maintaining compatibility with hydrophobic fiber materials

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite material principles by creating complex dye molecules composed of multiple functional components: diazo components, phthalimido-substituted aniline coupling components, and various substituent groups (R1-R9). This composite molecular structure combines the benefits of different chemical groups to achieve both excellent fastness properties and affinity for hydrophobic fibers

Inventive Principle:
Principle #40Composite materials

2Reliability

If dyes with improved fastness properties are developed, then the durability of dyeings is enhanced, but the complexity of dye preparation and synthesis increases

Engineering Contradiction:
Improvefastness to light, washing and perspirationVSAvoiddye synthesis process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies segmentation by dividing the complex dye molecule into distinct functional segments: the diazo component (Ar-NH2), the phthalimido-substituted aniline coupling component (formula 2), and various substituent groups. This segmentation allows for modular synthesis where each component can be prepared separately and then assembled through standardized diazotization and coupling reactions, simplifying the overall manufacturing process

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent uses intermediary compounds in the synthesis process. The phthalimido-substituted aniline coupling component serves as a key intermediary that facilitates the formation of the final azo dye structure. This intermediary approach allows for controlled reaction pathways and intermediate purification steps, making the overall synthesis more manageable despite the complexity of the final molecule

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If conventional azo dyes are used, then the dyeing process is straightforward, but the build-up performance in exhaust and thermosol processes is insufficient

Engineering Contradiction:
Improvebuild-up in exhaust and thermosol processesVSAvoiddye structure design precision
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent optimizes build-up performance by carefully adjusting structural parameters of the dye molecules. The alkyl chain lengths (C1-C12), positions of substituents (R1-R9), and types of functional groups are precisely controlled to enhance the dye's affinity for hydrophobic fibers and its performance in exhaust and thermosol processes, achieving excellent build-up without requiring complex application procedures

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2167496B1Azo dyes
Publication Date: 2014.09.24 HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
  • EP2167496B1 patent drawing
  • EP2167496B1 patent drawing
  • EP2167496B1 patent drawing

AI summary

The present invention relates to disperse azo dyes based on a phthalimido-substituted aniline coupling component and an aromatic-carbocyclic or an aromatic-heterocyclic diazo component, to a process for the preparation of such dyes and to their use in the dyeing or printing of semi-synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials.