Fluorinated Disperse Azo Dyes for Hot Light Fastness
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Solution Overview
Problem
Current disperse azo dyes used in dyeing hydrophobic fibre materials, particularly in the automotive industry, do not meet requirements for light fastness, especially hot light fastness, in dyeings or prints.
Innovation Solution
Development of disperse dyes with fluorine-containing substituents, specifically diazo components coupled with 2,6-diaminosubstituted pyridine derivatives, which are prepared through diazotization and coupling processes, offering improved light fastness and build-up in exhaust, thermosol processes, and textile printing.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional disperse azo dyes are used for dyeing hydrophobic fibre materials, then the dyeing process is simple and cost-effective, but the light fastness especially hot light fastness is insufficient
Solution Approach 1:
The patent modifies the molecular structure parameters of disperse azo dyes by introducing fluorine-containing substituents (R1 = fluoro, trifluoromethyl, trifluoromethoxy or trifluoromethylsulfonyl) at specific positions (R2 and R3) of the azo component. This structural parameter change enhances the light fastness and hot light fastness of the dyeings while maintaining the disperse dyeing process simplicity.
Solution Approach 2:
The patent creates composite dye molecules by coupling fluorine-containing diazo components with 2,6-diaminosubstituted pyridine coupling components. This composite structure combines the benefits of fluorine substitution (improved light fastness) with the coupling component (good build-up and dyeing properties), resolving the contradiction between performance improvement and structural complexity.
2Reliability
If dyes with improved light fastness are developed, then the fastness to light properties are enhanced, but the build-up in exhaust and thermosol processes may be affected
Solution Approach 1:
The patent applies fluorine-containing substituents at specific local positions (R2 and R3) of the azo component rather than throughout the entire molecule. This localized modification improves light fastness while minimizing interference with the dyeing mechanism and build-up properties in exhaust and thermosol processes.
Solution Approach 2:
The patent optimizes the fluorine substituent parameters (type and position) to achieve a balance between light fastness enhancement and maintaining good build-up characteristics. The specific fluorine-containing groups (fluoro, trifluoromethyl, etc.) are selected to provide the desired fastness without compromising dyeing efficiency.
3Reliability
If fluorine-containing substituents are introduced to improve light fastness, then the fastness properties are enhanced, but the manufacturing complexity increases
Solution Approach 1:
The patent uses commercially available or easily preparable fluorine-containing aniline derivatives as starting materials for diazotization. This preliminary preparation of the fluorine-substituted amine component simplifies the overall manufacturing process by eliminating the need to synthesize fluorine-containing intermediates from scratch.
Solution Approach 2:
The patent employs standard diazotization and coupling procedures with fluorine-containing substrates, maintaining the simplicity of the manufacturing process while achieving improved light fastness through molecular structure modification rather than process complexity.
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 provide excellent light fastness and build-up properties, ensuring high-quality dyeings with good fastness to light, thermofixing, chlorine, wetting, and rubbing, particularly in polyester materials, while maintaining minimal coloration of wool and cotton.
Implementation Method 1
a compound of formula (2) is diazotised in accordance with a customary procedure and then coupled to a coupling component of formula (3)
Implementation Method 2
The anilines of formula (2) are known or can be prepared according to known methods
Data Source
AI summary
The present invention relates to disperse azo dyes based on diazo components having at least one fluorine-containing substituent and an 2,6-diaminosubstituted pyridine coupling 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 fiber materials, more especially textile materials.