Anthrapyridone Sulfonic Acid Compounds for Inkjet Magenta Dyes
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Solution Overview
Problem
Magenta dyes for inkjet inks face challenges in achieving balanced light resistance, ozone resistance, water resistance, solubility, and long-term stability, with existing dyes often falling short in these properties, particularly in maintaining image quality under high humidity and exposure to oxidizing gases.
Innovation Solution
Anthrapyridone sulfonic acid compounds, either in their free acid form or as salts, are introduced with sulfonic acid substituents, which enhance water solubility and improve light and ozone resistance through specific structural modifications and synthesis methods, utilizing bromamine acid as a cost-effective starting material.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If anthrapyridone dyes without sulfonic groups are used, then brightness and light resistance are improved, but water solubility deteriorates
Solution Approach 1:
The patent applies local quality by introducing sulfonic acid groups at specific positions (5, 6, 7, or 8) on the anthrapyridone molecular scaffold. This localized modification allows the dye to maintain its core brightness and light resistance properties while gaining water solubility through the polar sulfonic groups. The selective positioning of sulfonic groups optimizes both solubility and color performance.
Solution Approach 2:
The patent creates a composite molecular structure combining the anthrapyridone core (providing brightness and light resistance) with sulfonic acid substituents (providing water solubility). This molecular-level composite achieves synergistic properties that neither component alone could provide, resolving the contradiction between solubility and light resistance.
2Stability of the object's composition
If H-acid derived azo dyes are used, then water resistance is improved, but light resistance and ozone resistance deteriorate
Solution Approach 1:
Instead of using the conventional H-acid derived azo dye structure, the patent inverts to an anthrapyridone-based structure with sulfonic acid groups. This structural inversion provides superior light resistance and ozone resistance while maintaining water resistance through the sulfonic groups, reversing the performance hierarchy of traditional dyes.
Solution Approach 2:
The patent changes the chemical parameters of the dye molecule by selecting specific substituents (A1, A2, R6, R7) on the anthrapyridone core, including electron-donating and electron-withdrawing groups at controlled positions. These parameter changes optimize the balance between water resistance, light resistance, and ozone resistance simultaneously.
3Reliability
If dyes are improved for light resistance, then ozone resistance improves, but solubility and long-term stability deteriorate
Solution Approach 1:
The patent applies local quality by strategically positioning sulfonic acid groups on the anthrapyridone scaffold. These localized polar groups enhance water solubility and long-term stability without compromising the extended conjugation system that provides light resistance. The specific positioning (5, 6, 7, or 8 positions) optimizes this local modification effect.
Solution Approach 2:
The patent creates a composite molecular architecture where the anthrapyridone core provides light and ozone resistance while the sulfonic acid substituents provide solubility and stability. This molecular composite resolves the contradiction by integrating complementary functions at different molecular regions.
4Manufacturing precision
If magenta dyes are used for inkjet inks, then image quality is improved, but resistance to oxidizing gases and moisture deteriorates
Solution Approach 1:
The patent converts the vulnerability of magenta dyes to oxidizing gases into a strength by incorporating sulfonic acid groups that provide ozone resistance. The electron-withdrawing nature of sulfonic groups stabilizes the dye molecule against oxidation while maintaining the vibrant magenta color quality, effectively converting the harm into a protective feature.
Solution Approach 2:
The patent changes the chemical parameters of the magenta dye by selecting specific electron-donating and electron-withdrawing substituents at controlled positions on the anthrapyridone core. These parameter changes enhance ozone and moisture resistance while preserving the desired image quality and color properties.
Data Source
AI summary
The present invention relates to a class of compounds of general formula (I) or their salts of general formula (II):In formula (I)-(II), the substituents (A)p and (SO3H)n on the benzene ring are at the ortho, meta or para position, n is 0-2, and p is 0-3; M is selected from Li+, Na+, K+, NH4+ or organic ammonium salt N+R1R2R3R4, where R1, R2, R3, R4 are the same or different H, C1-18 alkyl groups, cyclohexyl groups, CH2CH2OH, CH(CH3)CH2OH or benzyl groups; where p>0, A stands for the same or different groups selected from: H, CN, NO2, NH2, F, Cl, Br, C1-18 alkyl group, cyclohexyl group, phenyl group, benzyl group, phenoxy group, C1-18 alkoxy group, C1-18 alkylthio group, SO2CH═CH2, SO2CH2CH2A1, NR6COR5 or NR6SO2R5.