Diamino Pyrimidine Azo Dye Composition for Hot Light Fastness
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Solution Overview
Problem
Current diamino pyrimidine disperse azo dyes do not consistently meet modern requirements for light fastness, particularly in hot light fastness, necessitating the development of new dyes with improved properties.
Innovation Solution
Diamino pyrimidine disperse azo dyes substituted with a nitrogen-containing heterocyclic aromatic ring, which are synthesized through diazotization and coupling processes, offering enhanced light fastness properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If currently known diamino pyrimidine disperse azo dyes are used, 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 diamino pyrimidine disperse azo dyes by introducing nitrogen-containing heterocyclic aromatic rings at specific positions (R1, R2, R3, R4, or R5). This structural parameter change enhances light fastness and hot light fastness properties while maintaining the fundamental dyeing application process.
Solution Approach 2:
The invention creates composite molecular structures by combining diamino pyrimidine core with nitrogen-containing heterocyclic aromatic ring substituents. This composite approach integrates the beneficial properties of both structural elements to achieve superior light fastness without completely redesigning the entire dye molecule.
2Reliability
If diamino pyrimidine disperse azo dyes are used for dyeing synthetic hydrophobic fibre materials, then the dyeing process is efficient, but the color strength retention under heat-light exposure is insufficient
Solution Approach 1:
The patent introduces nitrogen-containing heterocyclic aromatic rings at specific local positions (R1, R2, R3, R4, or R5) on the diamino pyrimidine core structure. This localized modification targets specific areas of the molecule to enhance color strength retention under heat-light exposure without requiring complete restructuring of the entire dye molecule.
3Reliability
If new dyes with enhanced light fastness are developed, then the light fastness properties improve, but the dye structure becomes more complex
Solution Approach 1:
The patent systematically varies parameters such as the type of nitrogen-containing heterocyclic aromatic ring, its position on the pyrimidine core, and associated substituents (R1-R9) to optimize hot light fastness. This parameter-based approach allows for structured exploration of structure-property relationships while maintaining manageable molecular 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 resulting dyes exhibit excellent light fastness, heat fastness, and resistance to color change under heat-light exposure, outperforming existing dyes in terms of color strength retention and color change metrics.
Implementation Method 1
The present invention also relates to a process for the preparation an azo dye of formula (1), which comprises diazotizing an amine compound of formula (2a) or (3a) in accordance with a customary procedure, and then coupling the diazotized amine to a coupling component of formula (1a)
Data Source
AI summary
The present invention relates to azo dyes of formula (1), wherein D is a radical of formula (2) or (3), R1 and R2 independently denote hydrogen; C6–C10aryl which is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C1–C6alkyl, or C1–C6alkoxy; C1–C12alkyl which may be interrupted one or more times by -O-, -S-, -NR4-, -CO-, -COO- or –OOC-, and is unsubstituted or substituted by cyano, carboxy, hydroxy, C6–C10aryl, or C6–C10aryloxy, which C6–C10aryl or C6–C10aryloxy is unsubstituted or substituted by cyano, carboxy, hydroxy, halogen, C1–C6alkyl, or C1–C6alkoxy; R3 and R4 are each independently of the other hydrogen, halogen, nitro, cyano, trifluoromethyl, carboxy, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylcarbonyl, C6–C10arylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonylamino or C1-C4alkanoylamino; and R5 is halogen, nitro, cyano, trifluoromethyl, carboxy, C1-C6alkyl, C1-C6alkoxy, C1- C6alkylcarbonyl, C6–C10arylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonylamino or C1-C4alkanoylamino; and R6, R7, R8 and R9 independently of each other are hydrogen, hydroxy, halogen, cyano, nitro or C1-C4alkanoylamino, and the radicals X independently denote N or C-H, with the proviso that at least one radical X denotes C-H, which are distinguished by their good lightfastness properties.