Lipophilicity in dye-cellulose fibre binding

Abstract Lipophilicity in cellulose dyeing has been modelled by correlations of dye structural parameter with dye affinity and lipophilic dye parameters. In a series of anionic azo dyes hydrophobic interactions in dye-fibre binding only appeared in two subseries of dyes having a coupling component with one or two sulphonic groups. Good correlations with dye affinity and lipophilic paramaters were obtained by the Multiple Linear Regression (MLR) Analysis and Principal-Component-Regression (PCRA) approach. Minimum Steric Difference (MTD) calculations suggest the presence of mainly steric and possible electronic interactions in the adsorption of anionic azo dyes by cellulose fibre. Similar calculations were performed for a series of disperse azo dyes, suggesting possible electronic and hydrophobic effects in dye-fibre binding. Dye lipophilic properties also depend on polarity and bulk terms.

[1]  A. Bondi.  van der Waals Volumes and Radii , 1964 .

[2]  P. Mager,et al.  Non‐Least‐Squares Regression Analysis Applied to Organic and Medicinal Chemistry , 1994, Medicinal research reviews.

[3]  Walter Schmidt,et al.  A QSAR study of the adsorption by cellulose fibre of anthraquinone vat dyes , 1994 .

[4]  Svante Wold,et al.  Multivariate quantitative structure-activity relationships (QSAR): conditions for their applicability , 1983, J. Chem. Inf. Comput. Sci..

[5]  Bernard,et al.  Advances in Drug Research , 1964 .

[6]  H. Zollinger.  Color chemistry: Syntheses, properties, and applications of organic dyes and pigments , 1987 .

[7]  P. Carrupt,et al.  Solvent-dependent lipophilicity and hydrogen-bonding capacity of 2-pyridylalkanols , 1989 .

[8]  Rainer Franke,et al.  Theoretical drug design methods , 1984 .

[9]  K A Dill,et al.  The meaning of hydrophobicity. , 1990, Science.

[10]  H. Bach,et al.  Molekülbau und Haftung substantiver Farbstoffe auf Cellulose , 1963 .

[11]  A. Leo,et al.  Substituent constants for correlation analysis in chemistry and biology , 1979 .

[12]  Eric J. Lien,et al.  Physical Factors Contributing to Hydrophobic Constant π , 1986 .

[13]  Tudor I. Oprea,et al.  Multiconformational Minimal Steric Difference. Structure‐Acetylcholinesterase Hydrolysis Rates Relations for Acetic Acid Esters , 1993 .

[14]  E. Lien,et al.  Physical factors contributing to the partition coefficient and retention time of 2',3'-dideoxynucleoside analogues. , 1991, Journal of pharmaceutical sciences.