Quantitative Structure-Properties Relationship in Stilbene-Triazine Optical Brightener Design

Autor: Leszek Konopski, Ewa Wilkowska
Rok vydání: 2008
Předmět:
Zdroj: QSAR & Combinatorial Science. 27:357-364
ISSN: 1611-0218
1611-020X
DOI: 10.1002/qsar.200730027
Popis: The Quantitative Structure-Property Relationship (QSPR) has been studied in a group of bis(s-triazin-2-yl)-4,4′-diamino-2,2′-disulphostilbene Fluorescent Brightening Agents (FBAs). The degree of whiteness, tint and Yellowness Index (YI) were studied as parameters determining the brightening properties using surface-size press method on neutral printing papers, and the degree of whiteness W was chosen as the most appropriate for QSPR studies. The effectiveness of brightening depended on the substituent R in positions 4-(sulphophenylamino, disulphophenylamino or methoxy groups), and especially at position 6 of the triazine ring (disubstituted amino group NYZ). The best results were obtained when an amino acid moiety was built in the 6-substituent. Hammett electron constants and Taft induction constants were used as substituent descriptors. A quantitative correlation was found using simple and multiple regression analysis. The constructed model allowed to design two new brighteners containing R=2,5-disulphoaniline group, Y=H and Z=appropriately taurine and N-cyanoethyltaurine. To validate the model, the high values of whiteness predicted by the regression equation were confirmed by synthesis. The Taft σ*-constant values for CH(CH3)COOH and CH(CH2COOH)COOH substituents were calculated using the developed equation.
Databáze: OpenAIRE
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