Fibre-Reactive Azo Dye Composition for High Fixation and Wash-Off

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Solution Overview

Problem

Current reactive dyes used in textile dyeing lack sufficient substantivity, ease of washing off unfixed dye, tinctorial yield, and high reactivity, resulting in suboptimal dyeing properties such as light-fastness and wet-fastness.

Innovation Solution

Development of novel reactive dyes with specific molecular structures, including sulfo naphthalene or sulfo benzene groups and fibre-reactive groups, which enhance substantivity, fixing yields, and stability, allowing for high degrees of fixation and excellent fastness properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional reactive dyes are used, then the dyeing process can be performed, but the substantivity and fibre-dye bond stability are insufficient

Engineering Contradiction:
Improvefibre-dye bond stabilityVSAvoidease of washing off unfixed dye
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular structure of reactive dyes by introducing specific bridging members (aliphatic chains with hydroxyl groups) and combining different reactive groups (Z1 and Z2) with distinct mechanisms. This structural parameter change enhances fibre-dye bond stability while maintaining washability of unfixed dye through optimized molecular architecture.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite dye molecules that integrate multiple functional components: azo chromophores, sulfo naphthalene or sulfo benzene groups, aliphatic bridging members with hydroxyl groups, and dual fibre-reactive groups. This composite structure achieves both high bond stability and controlled wash-off properties.

Inventive Principle:
Principle #40Composite materials

2Productivity

If reactive dyes with high reactivity are used, then fixing yield improves, but ease of washing off unfixed dye deteriorates

Engineering Contradiction:
Improvefixing yieldVSAvoidease of washing off unfixed dye
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The dye molecule is segmented into distinct functional zones: chromophoric groups for colour, aliphatic bridging members with hydroxyl groups for fibre interaction, and dual fibre-reactive groups (Z1 and Z2) with different reactivity profiles. This segmentation allows high fixing yield through multiple reaction sites while enabling differential wash-off based on bond strength.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Different regions of the dye molecule possess different local properties: the fibre-reactive groups Z1 and Z2 have different reactivities and bond strengths, allowing one region to form strong stable bonds while another region forms bonds that are easier to hydrolyze during washing, thus achieving high fixing yield with manageable wash-off.

Inventive Principle:
Principle #3Local quality

3Reliability

If dyes with improved fixing properties are developed, then light-fastness and wet-fastness improve, but device complexity increases

Engineering Contradiction:
Improvelight-fastness and wet-fastnessVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent merges multiple known dye components into a single integrated molecular structure: azo chromophores, sulfo naphthalene or sulfo benzene groups, aliphatic bridging members with hydroxyl groups, and dual fibre-reactive groups. This merging achieves improved fastness properties through synergistic interactions while presenting a unified molecular architecture that can be synthesized through established chemical routes.

Inventive Principle:
Principle #5Merging (Combining)

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 reactive dyes exhibit high reactivity, good fixing capacity, and excellent fastness properties, including light-fastness and wet-fastness, with minimal soaping loss, making them suitable for a wide range of fibre materials, especially cotton.

Implementation Method 1

the novel dyes should especially be distinguished by high fixing yields and high fibre-dye bond stability

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

R6 is hydrogen, sulfo, halogen, carboxy, C1-C4 alkyl, C1-C4 alkoxy or a fibre-reactive group Z1 of the formula —SO2—Y (3a),—NH—CO—(CH2)l—SO2—Y (3b),—CONH—(CH2)m—SO2—Y (3c),—NH—CO—CH(Hal)—CH2-Hal (3d) or—NH—CO—C(Hal)=CH2 (3e)

Methodology Applied
Scientific EffectCovalent bonding: Chemical Bonding

Implementation Method 3

The dyes of formula (1) contain at least two, preferably from 2 to 5 and especially 4 or 5, sulfo groups, which are each present either in free acid form or, preferably, in salt form

Methodology Applied
Scientific EffectIonic interaction: Ion Repulsion/Attraction

Implementation Method 4

Dyeing nowadays requires reactive dyes that have sufficient substantivity

Methodology Applied
Scientific EffectAdsorption: Adsorption

Data Source

PatentUS8562694B2Fibre-reactive azo dyes, their preparation and their use
Publication Date: 2013.10.22 HUNTSMAN INTERNATIONAL LLC
  • US8562694B2 patent drawing
  • US8562694B2 patent drawing
  • US8562694B2 patent drawing

AI summary

Reactive dyes of the formula (1) wherein B is an aliphatic bridging member, G is a sulfo naphthalene group or a sulfo benzene group of the formula (2a) or a pyridone radical of the formula (2b), R1, R2, R3 and R4 are each independently of the others hydrogen or unsubstituted or substituted C1-C4alkyl, (R5)h denotes h identical or different substituents selected from the group sulfo, C1-C4alkyl and C1-C4alkoxy, R6 is hydrogen, sulfo, halogen, carboxy, C1-C4alkyl, C1-C4alkoxy or a fiber-reactive group Z1 of the formula —SO2—Y (3a), —NH—CO—(CH2)1—SO2—Y (3b), —CONH—(CH2)m—SO2—Y (3c), —NH—CO—CH(Hal)-CH2-Hal (3d) or —NH—CO—C(Hal)=CH2 (3e), R7 is amino, C1-C4alkyl or a fiber-reactive group Z2 of the formula —NH—(CH2)n—SO2—Y (3a), (R8)j denotes j identical or different substituents selected from the group sulfo, C2-C4alkanoylamino, ureido, C1-C4alkyl and C1-C4alkoxy, R9 is hydrogen, C1-C4alkyl or C1-C4alkoxy, R10 is hydrogen or C1-C4alkyl, R11 is hydrogen, cyano, carbamoyl or sulfomethyl, and R12 is hydrogen, C1-C4alkyl, or phenyl which is unsubstituted or substituted by C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, ureido, halogen or sulfo, X1 and X2 are halogen, Hal is chlorine or bromine, h and j are each independently of the other a number 0, 1 or 2; k is a number 1, 2 or 3; I, m and n are each independently of the other a number 2, 3 or 4, and Y is vinyl or a radical —CH2—CH2—U and U is a group removable under alkaline conditions, with the proviso that the dye of formula (1) contains at least one fiber-reactive group Z1 or Z2 are suitable for dyeing cellulosic or amide-group-containing fiber materials.