Anthraquinone Azo Dye Composition for High-Temperature Light Fastness

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Solution Overview

Problem

There is a need for new dyes or dye mixtures that yield strong, golden-yellow to orange shades with excellent build-up capacity and high temperature light fastness properties on semi-synthetic or synthetic hydrophobic fibre materials, particularly polyester textiles.

Innovation Solution

An azo dye formula combining a diazotised aminoanthraquinone with a specific coupling component, 1-butyl-3-cyano-6-hydroxy-2-pyridone, is synthesized and applied using known methods, offering high light fastness and resistance to pH variations, and can be mixed with other dyes for enhanced performance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional dyes are used on polyester, then dyeing can be achieved, but the light fastness deteriorates at high temperature

Engineering Contradiction:
Improvelight fastnessVSAvoidhigh temperature light fastness
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the dye molecules, specifically incorporating cyano groups at positions 5 and 8 of the anthraquinone nucleus, and using specific coupling components with electron-withdrawing groups. These structural parameter changes result in dyes that maintain excellent light fastness (grade 5-7) even under high temperature conditions (up to 200°C thermofixing), resolving the contradiction between achieving adequate light fastness and maintaining it at elevated temperatures.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If dye mixtures are used to achieve desired shades, then colour variety is improved, but the build-up capacity deteriorates

Engineering Contradiction:
Improveshade varietyVSAvoidbuild-up capacity
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent achieves universality by developing a series of dyes based on the same core structure (1,4,5,8-substituted anthraquinones with cyano groups) that can produce multiple shades from golden-yellow to orange by varying only the coupling component. This allows single-dye applications with excellent build-up capacity (up to 70% exhaustion) while maintaining shade variety, eliminating the need for complex dye mixtures that would compromise build-up performance.

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Quantity of substance

If strong dyes are used to achieve intense colour, then tinctorial strength is improved, but fastness to migration deteriorates

Engineering Contradiction:
Improvecolour strengthVSAvoidfastness to migration
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent applies composite material principles by creating complex molecular structures that combine multiple functional groups: the anthraquinone chromophore for colour strength, cyano groups at positions 5 and 8 for fastness properties, and specifically designed coupling components (such as pyridone derivatives with electron-withdrawing groups) for migration resistance. This composite molecular architecture achieves both intense colouration (exhaustion up to 70%) and excellent fastness to migration (grade 5-7), resolving the contradiction between tinctorial strength and migration fastness.

Inventive Principle:
Principle #40Composite materials

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 azo dye provides strong, level colour shades with excellent fastness to light, thermofixing, pleating, chlorine, water, perspiration, and washing, suitable for various textile materials including polyester, while maintaining good build-up characteristics and high temperature light fastness.

Implementation Method 1

subsequently coupling the resulting diazonium salt to the coupling component of the formula (6a)

Methodology Applied
Scientific EffectAzo coupling: Chemical Bonding

Implementation Method 2

yield tinctorially strong dyeings or prints in a golden-yellow to orange shades

Methodology Applied
Scientific EffectLight absorption: Absorption (EM radiation)

Data Source

PatentEP2859051B1Anthraquinone azo dyes
Publication Date: 2019.04.17 HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
  • EP2859051B1 patent drawing
  • EP2859051B1 patent drawing
  • EP2859051B1 patent drawing

AI summary

The present invention relates to azo dyes of the formula (1), wherein R1 is hydrogen or hydroxy, R2 is hydrogen or hydroxy, at least one of the radicals R1 and R2 being hydroxy, R3 is hydrogen, cyano, nitro or halogen, R4 is hydrogen, cyano, nitro or halogen, D represents a radical of the formula (2) or (3), wherein R5 denotes C1-C12alkyl, C1-C12hydroxyalkyl, C1-C12alkoxyalkyl, C2-C12alkenyl, C6-C30aryl or C7-C36aralkyl and R6 and R7, each independently of the other, is hydrogen, C1-C12alkyl, C1-C12hydroxyalkyl, C1C12alkoxyalkyl, C6-C30aryl or C7-C36aralkyl, with the proviso that the compound of formula (1) is excluded, wherein R1 is hydrogen, R2 is hydroxy, R3 and R4 is hydrogen and D is the radical of formula (2) wherein R5 is ethyl, and to the use of those dye mixtures in the dyeing or printing of semi-synthetic or synthetic hydrophobic fibre materials.