Reactive dye compound and preparation method and application thereof
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Solution Overview
Problem
Reactive dyes used for printing and dyeing cellulosic and polyamide fibers face issues with washing fastness due to hydrolysis of covalent bonds, leading to poor durability of the dyed fabrics.
Innovation Solution
Development of reactive dye compounds with a novel structure incorporating 3,5-dihydroxybenzoic acid, which involves diazotization and coupling reactions to create compounds with improved fiber-reactive groups, resulting in enhanced stability and fastness.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional reactive dyes are used for printing and dyeing cellulosic and polyamide fibers, then the dyeing process is simple and cost-effective, but the washing fastness deteriorates due to hydrolysis of covalent bonds
Solution Approach 1:
The patent applies composite materials by combining multiple functional groups within the dye molecule: a novel coupler structure (3,5-dihydroxybenzoic acid derivative) combined with reactive groups (vinyl sulfone, beta-sulfatoethyl sulfone, or chlorotriazine). This composite molecular structure integrates both strong fiber bonding capability and hydrolysis resistance, achieving excellent washing fastness while maintaining practical dyeing application
Solution Approach 2:
The patent employs parameter changes by modifying the chemical structure parameters of the dye molecule - specifically introducing the novel coupler with 3,5-dihydroxybenzoic acid structure and combining it with different reactive group types. This structural parameter modification fundamentally changes the bond stability parameter, making the covalent bonds resistant to hydrolysis while maintaining dyeing effectiveness
2Stability of the object's composition
If reactive dye compounds with improved fiber-reactive groups are developed, then fiber-bonding stability improves, but the manufacturing complexity increases
Solution Approach 1:
The patent applies segmentation by dividing the dye molecule into distinct functional segments: the novel coupler segment (3,5-dihydroxybenzoic acid derivative), the azo chromophore segment, and the reactive group segment. This segmentation allows each part to be optimized independently for its specific function while simplifying the overall synthesis pathway through modular assembly of these segments
Solution Approach 2:
The patent uses intermediaries in the form of pre-synthesized coupling components and diazo components that can be readily combined. These intermediary compounds serve as building blocks that simplify the final dye synthesis step, making the manufacturing process more manageable despite the complexity of the final molecular structure
3Productivity
If conventional reactive dyes are used, then the dyeing process is straightforward, but build-up properties and clarity of remanent dyeing liquor are insufficient
Solution Approach 1:
The patent employs parameter changes by modifying the molecular weight, chromophore structure, and reactive group type parameters of the dye. These parameter changes directly improve build-up properties (the ability to achieve deep, uniform colors) and clarify the remanent dyeing liquor (reducing residue), while the systematic approach to structural modification keeps the synthesis process manageable
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 reactive dye compounds demonstrate excellent washing fastness, fiber-bonding stability, and build-up properties, suitable for a wide range of fibers including cotton, rayon, silk, and wool, with high fixation rates and reduced residue.
Implementation Method 1
Covalent bonds between some reactive dyes and cotton fibers are affected by external conditions and prone to being broken and hydrolysis
Implementation Method 2
Covalent bonds between some reactive dyes and cotton fibers are affected by external conditions and prone to being broken and hydrolysis
Data Source
AI summary
A reactive dye compound and preparation method and application for printing and dyeing of cellulosic fibers, polyamide fibers and fabrics thereof. Formula (I) is the dye compound structure where D1 and D2 are each independently the group of the following formula (a) or (b) or (c), and D1 and D2 are not simultaneously selected from the following formula (a). R1, R2, R4, R5, R7 and R8 are each independently H, linear or branched C1˜C4 alkyl, C1˜C4 alkoxy or sulfo; m=0-3. Each R3 is independently selected from amino, sulfo, ureido, C1˜C4 alkyl, C1˜C4 alkanoylamino or C1˜C4 alkoxy, n=0-3, and each R6 is independently selected from hydroxyl, amino and sulfo. X1, X2 and X3 are each independently H, C1˜C4 alkyl, C1˜C4 alkoxy, —SO2Y1, —NHCO(CH2)pSO2Y2 or —CONH(CH2)qSO2Y3, and at least one of D1 and D2 contains a fiber-reactive group. Y1˜Y3 are each independently —CH═CH2, —C2H4OSO3H or —CH2CH2Cl, p=1-3, and q=1-3.