Fluorescent reactive dyes, process for the production thereof and their use

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Solution Overview

Problem

Fluorescent reactive dyes used for dyeing and printing hydroxyl-, amino-, and/or carboxamido-containing materials suffer from unsatisfactory light fastness and limitations in build-up and other dyeing properties, especially in exhaust processes.

Innovation Solution

Development of dyes with two or more reactive anchors, specifically designed with certain chromophore structures and spacers, which enhance fluorescent properties and fastness when used alone or in combination with other fluorescent dyes on these materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If conventional fluorescent reactive dyes are used, then fluorescent properties are achieved, but light fastness is unsatisfactory

Engineering Contradiction:
Improvefluorescent propertiesVSAvoidlight fastness
Core Design Contradiction:
Illumination intensityVSReliability

Solution Approach 1:

The patent employs composite dye molecules containing both fluorescent chromophore units and reactive anchor units. This composite structure allows the dye to simultaneously exhibit fluorescent properties and form stable covalent bonds with fiber substrates, thereby achieving both bright fluorescence and improved light fastness that conventional single-function dyes cannot provide.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The dye molecule is segmented into distinct functional units: fluorescent chromophore units (providing optical properties) and reactive anchor units (providing bonding capability). This segmentation allows each unit to perform its specific function independently while contributing to the overall performance, resolving the contradiction between fluorescence and fastness.

Inventive Principle:
Principle #1Segmentation

2Illumination intensity

If conventional fluorescent reactive dyes are used, then fluorescent properties are achieved, but build-up and dyeing properties are limited

Engineering Contradiction:
Improvefluorescent propertiesVSAvoidbuild-up and dyeing properties
Core Design Contradiction:
Illumination intensityVSProductivity

Solution Approach 1:

The reactive anchor units in the patent's dye molecules are designed to be universally reactive with multiple types of fiber substrates containing hydroxyl, amino, and/or carboxamido groups. This multi-functionality enables the dye to effectively dye various natural and synthetic fibers, significantly improving build-up and dyeing properties across different material types while maintaining fluorescent characteristics.

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

3Reliability

If dyes with reactive anchors are introduced, then fastness properties improve, but dyeing performance may be affected

Engineering Contradiction:
Improvefastness propertiesVSAvoiddyeing performance
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent optimizes parameters including the number and positioning of reactive anchor units, the structure of spacer units connecting chromophores to anchors, and the chemical composition of the chromophore units. These parameter changes enable the dye to achieve optimal balance between fastness (through sufficient reactive anchors) and dyeing performance (through appropriate spacer design and chromophore reactivity).

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 dyes exhibit improved fluorescent properties and overall fastness on hydroxyl-, amino-, and/or carboxamido-containing materials, offering better build-up and dyeing performance compared to existing dyes.

Implementation Method 1

This can be achieved with groups having activated leaving groups, such as halogen or OSO 3 H, which can be replaced in a nucleophilic substitution reaction by the hydroxyl-, amino-and/or carboxamido-containing fibre.

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 2

A second reaction type to form a covalent bond to hydroxyl-, amino- and/or carboxamido-containing material is the nucleophilic addition to an activated carbon-carbon double bond by the hydroxyl-, amino- groups of the fibre.

Methodology Applied
Scientific EffectNucleophilic addition: Chemical Bonding

Implementation Method 3

Fluorescent reactive dyes are known from prior art and can be used as colorants in different applications

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Data Source

PatentEP3131974B1Fluorescent reactive dyes, process for the production thereof and their use
Publication Date: 2018.01.03 DYSTAR COLOURS DISTRIBUTION GMBH
  • EP3131974B1 patent drawing
  • EP3131974B1 patent drawing
  • EP3131974B1 patent drawing

AI summary

The present invention is directed to fluorescent reactive dyes of general formula (I) a process for the production thereof and their use.