Fibre-Reactive Azo Dye Composition for High Fixing and Wash-Off
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Solution Overview
Problem
Current reactive dyes for 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 a specific chemical structure, including a radical of -CH2-CH(R12)- or -(R12)CH-CH2-, where R12 is C1-C4 alkyl, and fibre-reactive groups, allowing for high fixing yields and fibre-dye bond stability, along with a process involving cyanuric halides and diazotization reactions to produce monoazo compounds with improved dyeing properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional reactive dyes are used, then the dyeing process can be performed with existing materials, but the dyeings do not achieve sufficient substantivity, tinctorial yield, or fibre-dye bond stability
Solution Approach 1:
The patent modifies the molecular structure of reactive dyes by introducing specific radical groups (B with -CH2-CH(R12)- structure, Z1 as fibre-reactive group, R7 as amino, RB as C2-C4 alkanoylamino or ureido) and adjusting parameters like k (2 or 3) and l (2 or 3) to optimize the balance between fibre-dye bond stability and ease of manufacture. These structural parameter changes enable high substantivity and tinctorial yield while maintaining manufacturability through established chemical synthesis routes.
Solution Approach 2:
The invention creates composite dye molecules combining multiple functional groups (azo chromophore, fibre-reactive groups Z1 and Z2, amino groups R7, and alkanoylamino/ureido groups RB) into a unified molecular structure. This composite structure integrates substantivity, reactivity, and fastness properties within a single dye molecule, resolving the contradiction between achieving high fibre-dye bond stability and maintaining ease of manufacture.
2Productivity
If reactive dyes with high reactivity are used, then fixing yields improve, but ease of washing off unfixed dye deteriorates
Solution Approach 1:
The patent applies local quality by differentiating the functions of different parts of the dye molecule: the fibre-reactive groups (Z1 and Z2) are designed to react strongly with fibre for high fixing yield, while the hydrophilic groups (sulfo groups R5 and their salts) are positioned to provide water solubility for easy washing of unfixed dye. This spatial and functional differentiation within the molecular structure resolves the contradiction between high reactivity and ease of washing.
Solution Approach 2:
The invention adjusts the parameter of hydrophilicity through the inclusion of 2 to 4 sulfo groups (R5) in free acid or salt form, which can be adjusted independently of the reactive group parameters (k and l). This allows optimization of fixing yield through reactive group configuration while maintaining ease of washing through controlled hydrophilicity from sulfo groups.
3Productivity
If conventional dye structures are used, then manufacturing simplicity is maintained, but tinctorial yield and reactivity are insufficient
Solution Approach 1:
The patent systematically varies molecular parameters (k = 2 or 3, l = 2 or 3, R12 = C1-C4 alkyl, RB = C2-C4 alkanoylamino or ureido) within a defined structural framework to optimize tinctorial yield and reactivity. These controlled parameter changes within established chemical families maintain manufacturing simplicity while achieving superior performance compared to conventional structures.
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 novel reactive dyes exhibit high reactivity, excellent fixing capacity, and superior fastness properties, including high tinctorial strength and stability, with low soaping loss and excellent light and wet-fastness, making them suitable for a wide range of fibre materials.
Implementation Method 1
Z1 is a fibre-reactive group of the formula -SO2-Y (3a) or -NH-CO-(CH2)l-SO2-Y (3b)... high fixing yields and high fibre-dye bond stability
Implementation Method 2
Diazotisation is carried out in customary manner, for example by diazotising in a mineral acid solution, for example a hydrochloric-acid-containing solution, with a nitrite, for example sodium nitrite, at a low temperature, for example from 0 to 30°C
Implementation Method 3
then coupling with the appropriate coupling component in a neutral to slightly acidic medium, for example at a pH from 3 to 7 and at low temperatures, for example from 0 to 30°C
Implementation Method 4
the compounds of formulae (6) and (7) are reacted with one another in a suitable order... cyanuric halides and diazotization reactions to produce monoazo compounds
Data Source
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 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), R7 is amino, C1-C4alkyl or a fibre-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 fibre-reactive group Z1 or Z2 are suitable for dyeing cellulosic or amide-group-containing fibre materials.