Steric and electrostatic effects in dye-cellulose interactions by the MTD and CoMFA approaches

This paper presents the application of the MTD (minimal steric difference) analysis and CoMFA (comparative molecular field analysis) to series of anthraquinone vat, mono and disazo and disperses dyes with known affinities for cellulose fiber. A comparison of the results demonstrates that these methods usually agree with the prediction of structural features favorable for dyeing. A series of n =49 anthraquinone vat dyes was studied by MTD with r 2 between 0.903 and 0.941 and r CV 2 values in the range of 0.827-0.878. For CoMFA, r 2 =0.992, r CV 2 =0.841 were obtained; the CoMFA field is in rather good agreement with vertex attributions, by MTD for attractive and repulsive vertices. Anionic disazo dyes were studied by the CoMFA method ( n =21, r 2 =0.999, r CV 2 =0.703). Monoazo dyes (several series) were studied by CoMFA and MTD. The effect of lipophilicity on dye fiber affinity was, also, studied for these dyes. Disperse dye adsorption was analyzed by MTD and CoMFA ( n =27, r 2 =0.925, r CV 2 =0.776). Conclusions refer to the effect of structural features of dye molecules upon adsorption on cellulose fibers.

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

[2]  Sorel Muresan,et al.  Multiple Linear Regression (MLR) and Neural Network (NN) calculations of some disazo dye adsorption on cellulose , 1997 .

[3]  P. J. Cox.  Kirk-Othmer Encyclopedia of Chemical Technology, 4th edn., J.I. Kroschwitz, M. Howe-Grant (Eds.), in: Imaging Technology to Lanthanides, Volume 14. Wiley, New York (1995), xxviii, 0-471-52683-5 , 1996 .

[4]  Walter M. F. Fabian,et al.  Structure‐Affinity Binding Relationships by Principal‐Component‐Regression Analysis of Anthraquinone Dyes , 1995 .

[5]  H. Kubinyi.  Comparative Molecular Field Analysis (CoMFA) , 2002 .

[6]  Walter M. F. Fabian,et al.  Comparative molecular field analysis (CoMFA) of dye-fibre affinities. Part 2. Symmetrical bisazo dyes , 1996 .

[7]  Walter Schmidt,et al.  Lipophilicity in dye-cellulose fibre binding , 1996 .

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

[9]  R. Cramer,et al.  Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. , 1988, Journal of the American Chemical Society.

[10]  Walter M. F. Fabian,et al.  Comparative Molecular Field Analysis of Heterocyclic Monoazo Dye-Fiber Affinities , 1998, J. Chem. Inf. Comput. Sci..

[11]  Walter Schmidt,et al.  Structure-affinity binding relationships of some 4-aminoazobenzene derivatives for cellulose fibre , 1995 .

[12]  J. Hearle.  CHAPTER 19 – STRUCTURE, PROPERTIES, AND USES , 1963 .

[13]  B. Skagerberg,et al.  Comparison of Chemometric Models for QSAR , 1990 .

[14]  Walter M. F. Fabian,et al.  Comparative molecular field analysis (CoMFA), semiempirical (AM1) molecular orbital and multiconformational minimal steric difference (MTD) calculations of anthraquinone dye-fibre affinities , 1995 .

[15]  Z. Simon,et al.  Structure-activity Relations in Gestagenic Steroids by the MTD Method. The Case of Hard Molecules and Soft Receptors , 1992 .

[16]  Tudor I. Oprea,et al.  QSAR studies of disperse azo dyes. Towards the negation of the pharmacophore theory of dye-fiber interaction? , 1997 .