Basic Bisazo Compounds for Dye Fastness and Stability
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Solution Overview
Problem
Current disazo pyridone dyes lack improved properties for dyeing paper, textiles, and leather, particularly in terms of fastness and environmental impact.
Innovation Solution
Development of specific basic bisazo compounds with defined alkyl and aryl groups, allowing for improved dye properties through specific structural formulations and processes, including diazotization and coupling reactions, followed by conversion into stable salt forms for enhanced stability and solubility.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional disazo pyridone dyes are used, then dyeing of paper, textiles and leather is achieved, but fastness properties and environmental performance are insufficient
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure of disazo pyridone dyes through specific substitutions at defined positions (R1-R14 groups) to achieve improved fastness properties and reduced environmental impact. The systematic variation of structural parameters leads to enhanced light fastness, wet fastness, and alcohol fastness while minimizing wastewater coloration.
Solution Approach 2:
The invention creates composite dye structures by combining disazo pyridone core structures with various substituent groups (alkyl, aryl, heteroaryl, and their substituted forms). These composite molecular structures integrate multiple functional groups that collectively provide both improved fastness properties and reduced environmental harm.
2Reliability
If basic bisazo compounds are synthesized through diazotization and coupling reactions, then improved fastness properties are achieved, but process complexity increases
Solution Approach 1:
The patent applies preliminary action by pre-synthesizing and isolating the diamine components (formula II) and diazonium salts (formula III) before the final coupling reaction. This stepwise approach allows for better control of each reaction stage, ensuring improved fastness properties while managing process complexity through systematic preparation of intermediates.
Solution Approach 2:
The synthesis process is segmented into distinct stages: (1) formation of diamine components, (2) diazotization to form diazonium salts, and (3) coupling reactions to form the final bisazo compounds. This segmentation allows each step to be optimized independently, achieving superior fastness properties while maintaining manageable process complexity.
3Stability of the object's composition
If compounds are converted into salt forms, then solubility and stability are improved, but additional processing steps are required
Solution Approach 1:
The patent applies parameter changes by converting the basic bisazo compounds into their salt forms (acid addition salts) to improve solubility and stability. This chemical modification changes the physical and chemical parameters of the dye molecules, enhancing their performance characteristics while the salt formation process itself is a straightforward, well-established procedure.
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 compounds exhibit excellent fastness properties, including light, wet, and alcohol fastness, with improved solubility and stability, reducing environmental impact by minimizing wastewater coloration and maintaining dye strength across various substrates.
Implementation Method 1
reacting the bis-diazonium salt of a di-amine of formula (II), with one equivalent compound of formula (III) and one equivalent compound of formula (III')
Implementation Method 2
Diazotisation and coupling may be effected in accordance with conventional methods. The coupling reaction advantageously is carried out in an aqueous reaction medium
Implementation Method 3
The reaction mixtures comprising compounds of formula (I) thus obtained may be converted into stable liquid formulations with improved long term stability by desalting by ultra filtration
Implementation Method 4
The compounds of formula (I) containing free basic groups may be converted wholly or in part into water-soluble salts by reacting with any inorganic or organic acids
Data Source
AI summary
The invention relates to basic bisazo compounds according to formula (I) wherein all substituents are defined as in Claim 1, their production, their use as dyestuffs as well as material dyed with these dyestuffs.