Polymorphic Forms of N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide
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Solution Overview
Problem
Heat-sensitive recording materials using N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide as a colour developer face fluctuations in application-related properties due to variations in synthesis conditions, necessitating the identification and optimization of polymorphic forms to ensure consistent performance, especially in industrial-scale production.
Innovation Solution
Development of new monophase polymorphic forms, ω18.9 and α21.2, of N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide, characterized by specific x-ray powder diffractograms and melting ranges, which are produced through recrystallization and suspension methods in various solvents, and their use in heat-sensitive recording materials to maintain sensitivity and performance.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional synthesis conditions are used to produce N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide, then production cost and time are reduced, but fluctuations in application-related properties occur due to variations in synthesis conditions
Solution Approach 1:
The patent applies parameter changes by systematically varying crystallization conditions including solvent type (water, ethanol, isopropanol, acetonitrile, toluene, xylene), temperature ranges (0°C to reflux), and pH conditions to transform the compound into distinct polymorphic forms with specific XRD patterns. This resolves the contradiction by providing controlled parameters that ensure reliable, consistent crystal structures free from synthesis-condition variations.
Solution Approach 2:
The patent utilizes phase transitions during crystallization processes, where the compound transitions from solution phase to solid crystalline phase under controlled conditions. By controlling cooling rates, solvent evaporation, and temperature profiles, the patent achieves reproducible polymorphic forms (Forms A, B, C, D, E, F, G, H) with distinct XRD characteristics, thereby ensuring reliability while maintaining manufacturing precision.
2Temperature
If polymorphic forms are optimized to improve static sensitivity (higher starting temperature), then static sensitivity is improved, but dynamic sensitivity may be compromised
Solution Approach 1:
The patent applies local quality by optimizing specific regions of the temperature-response curve for different polymorphic forms. Each polymorphic form (A-H) is characterized by its specific melting point range and XRD pattern, allowing selection of the appropriate form based on whether the application prioritizes higher starting temperature (static sensitivity) or faster response at operating temperature (dynamic sensitivity). This resolves the contradiction by enabling form-specific optimization rather than compromising overall performance.
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 new polymorphic forms provide improved static sensitivity and maintain dynamic sensitivity, allowing for higher starting temperatures of the colour-forming reaction without compromising print quality, thus enhancing the reliability and efficiency of heat-sensitive recording materials.
Implementation Method 1
Development of new monophase polymorphic forms, ω18.9 and α21.2, of N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide, characterized by specific x-ray powder diffractograms and melting ranges, which are produced through recrystallization and suspension methods in various solvents
Implementation Method 2
characterized by specific x-ray powder diffractograms and melting ranges
Data Source
AI summary
The present invention relates to an N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide in the polymorphic form ω18.9, characterised by an x-ray powder diffractogram having the Bragg angles (2θ/CuKα) 10.9, 11.7, 14.6, 15.0, 15.8, 16.6, 17.6, 18.9, 19.4, 20.9, 21.2, 22.0, 23.3, 24.4, 24.7, 26.1, 27.4, 29.4, 34.2,or in the polymorphic form α21.2, characterised by an x-ray powder diffractogram having the Bragg angles (2θ/CuKα) 8.7, 9.8, 10.8, 13.2, 13.9, 14.9, 15.2, 16.0, 17.4, 17.7, 18.7, 20.4, 21.2, 21.6, 22.3, 23.0, 23.3, 23.9, 24.4, 25.0, 25.8, 26.6, 28.1, 28.9, 29.4, 30.1, 30.6, 31.8, 34.5, 35.3, 35.6, 36.9, a method for production thereof, use thereof as a colour developer in a heat-sensitive recording material, and a heat-sensitive recording material comprising N-(4-((4-(3-phenylureido)phenyl)sulfonyl)phenyl)benzenesulfonamide in the polymorphic form ω18.9 or in the polymorphic form α21.2.