Reactive Disperse AZO Dye Structure for Stable Supercritical CO2 Dyeing

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Solution Overview

Problem

Reactive disperse dyes used in supercritical CO2 for natural fiber dyeing often suffer from undesirable electron cloud interactions due to active groups, affecting dye coloring and stability.

Innovation Solution

A reactive disperse dye with a specific structure, incorporating a longer alkane-chain bridging group between the chromophoric parent structure and a cyanuric chloride active group, is developed to enhance electron cloud donation-withdrawal effects, improving color stability and compatibility with supercritical fluids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If a reactive group is attached to the parent structure of a disperse dye to enable dyeing of natural fibers in supercritical CO2, then the dye can react with reactive groups in natural fibers, but the active group itself and its reaction have undesirable influence on the dye coloring system

Engineering Contradiction:
Improvedyeing capability on natural fibersVSAvoidcolor stability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The dye molecule is segmented into distinct functional regions: a chromophoric parent structure for color, a reactive group for fiber bonding, and an electron-donating substituent on the coupling component to modulate electron cloud density. This segmentation allows each component to perform its specific function while minimizing interference between them, particularly reducing the negative impact of the reactive group on color stability.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent applies local quality by introducing specific substituents (electron-donating groups) at specific locations (coupling component) of the dye molecule. This localized modification enhances electron cloud density in the conjugated system at the coupling site, which compensates for electron withdrawal by the reactive group, thereby maintaining overall color stability while preserving reactivity with natural fibers.

Inventive Principle:
Principle #3Local quality

2Ease of manufacture

If simple reactive disperse dye structures are used, then the dye can be applied to dyeing of natural fibers in supercritical CO2, but the structure has undesirable donating/withdrawing effect of the coupling component on the electron cloud in the conjugated system

Engineering Contradiction:
Improvedye synthesis simplicityVSAvoidelectron cloud density control
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the dye structure by introducing electron-donating substituents (such as alkyl groups, hydroxyl groups, or amino groups) on the coupling component. This parameter change directly affects the electron cloud density in the conjugated system, compensating for electron withdrawal by the reactive group and improving color stability without complicating the manufacturing process.

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 dye structure reduces the influence of active groups on the dye system, enhancing hyperchromic effect, color stability, and compatibility with supercritical CO2, while maintaining excellent reaction controllability and low production costs.

Implementation Method 1

The reactive disperse dye is a specially structured dye which can be dissolved in non-polar supercritical CO2 fluid, and react with reactive groups in natural fibers

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

supercritical CO2 fluid not only has the characteristics of low viscosity, high diffusivity

Methodology Applied
Scientific EffectDiffusion: Diffusion

Data Source

PatentUS11193024B2AZO dye for waterless dyeing of natural fibers in supercritical CO<sub>2 </sub>fluid, and preparation method thereof
Publication Date: 2021.12.07 JIANGSU DANMAO TEXTILE
  • US11193024B2 patent drawing
  • US11193024B2 patent drawing
  • US11193024B2 patent drawing

AI summary

The invention discloses a special-purpose reactive disperse dye for waterless dyeing of natural fibers in supercritical CO2 fluid and an intermediate thereof. The reactive disperse dye has a longer alkane-chain bridging group between a chromophoric parent structure and an active group of the dye, which effectively promotes the donating-withdrawing effect on the electron cloud in the conjugated system, enhances the hyperchromic effect, effectively reduce the influence of the active group itself and its reaction on the dye coloring system, improves the color and stability against acid and alkali of the dye, and facilitate the improvement of the compatibility of the dye with supercritical fluid and the dyeing performance for natural fibers as well. The invention also discloses an intermediate of the reactive disperse dye, and a method for preparing the reactive disperse dye.