DYES AND PIGMENTS: NEW RESEARCH No part of this digital document may be reproduced, stored in a retrieval system or transmitted in any form or by any means. The publisher has taken reasonable care in the preparation of this digital document, but makes no expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions. No liability is assumed for incidental or consequential damages in connection with or arising out of information contained herein. This digital document is sold with the clear understanding that the publisher is not engaged in rendering legal, medical or any other professional services. DYES AND PIGMENTS: NEW RESEARCH ARNOLD R. LANG EDITOR Nova Science Publishers, Inc. New York Copyright © 2009 by Nova Science Publishers, Inc. All rights reserved. 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LIBRARY OF CONGRESS CATALOGING-IN-PUBLICATION DATA Dyes & pigments : new research / [edited by] Arnold R. Lang. p. cm. ISBN 978-1-60876-195-1 (E-Book) 1. Dyes and dyeing. 2. Pigments. I. Lang, Arnold R. II. Title: Dyes and pigments. TP910.D96 2008 667'.2--dc22 2008031082 Published by Nova Science Publishers, Inc. Ô New York CONTENTS Preface vii Chapter 1 Photodynamic Therapy 1 Petr Zimcik and Miroslav Miletin Chapter 2 Phthlocyanine to Use Photosensitizer for Photodynamic Therapy of Cancer 63 Keiichi Skamoto and Eiko Ohno-Okumura Chapter 3 Dyes, Pigments and Supercritical Fluids: Selection of Emerging Applications 97 M. D. Gordillo, C. Pereyra and E. J. Martínez de la Ossa Chapter 4 Photo-Controlled Molecular Switches Based on Photochromic Spirooxazine Dyes 111 Sung-Hoon Kim and Sheng Wang Chapter 5 Combined Sonohomogeneous and Heterogeneous Oxidation of Dyes for Wastewater Treatment 143 Ewere Odaro and Shaobin Wang Chapter 6 Decoloration of Textile Wastewaters 175 Julija Volmajer Valh and Alenka Majcen Le Marechal Chapter 7 Non-conventional Sorbents for the Dye Removal from Waters: Mechanisms and Selected Applications 201 Pavel Janoš Chapter 8 Irradiation Treatment of Azo Dyes in Aqueous Solution 225 László Wojnárovits and Erzsébet Takács Chapter 9 Application of Advanced Oxidation Processes (AOP) to Dye Degradation - An Overview 259 M. A. Rauf and S. Salman Ashraf Chapter 10 First Steps to a Deductive Classification System of Colorants from the Point of View of Structural Chemistry 291 G. Lincke vi Contents Chapter 11 Removal of Dyes from Solution on Clay Surfaces - An Overview 309 M. A. Rauf Chapter 12 The Beauty of Colors: The Yellow Flavonols in Science and Art 331 Aldo Romani Chapter 13 Inorganic Pigments to Colour Ceramic Materials: State of the Art and Future Trends 351 Federica Bondioli Chapter 14 Synthesis and Characterization of Several Series of Substituted Metallophthalocyanines 369 Fangdi Cong, Xiguang Du, Jianxin Li, Dongliang Tian and Wenjuan Duan Chapter 15 Dyes and Pigments with Ecologically More Tolerant Application 383 T. N. Konstantinova and P. P. Miladinova Chapter 16 Enhanced Anthraquinone Dye Production in Plant Cell Cultures of Rubiaceae Species: Emerging Role of Signaling Pathways 403 Norbert Orbán, Imre Boldizsár and Károly Bóka Short Commentary 421 The Use of Solid Media for Bacterial Growth in Degradation of Dyes 421 Carlos Costa, Blanca E. Barragán and M. Carmen Márquez Index 433 PREFACE Chapter 1 - Photodynamic therapy (PDT) is a cancer treatment based on activation of a drug by light. The drug, called photosensitizer, absorbs the energy of light of the proper wavelength and transfers it to surrounding molecules, mainly oxygen, forming reactive oxygen forms like radicals and singlet oxygen. These highly reactive species are responsible for destruction of targeted cells. Besides the direct effect on the cells, vascular shutdown develops as well and immune response is activated, both being important for long-term control over the tumor. Most of the photosensitizers are recruited from the group of porphyrins and related compounds like chlorins, bacteriochlorins, porphycenes, texaphyrins, and phthalocyanines. However, other dyes also entered the trials for photodynamic evaluation, e.g. some tricyclic dyes or hypericine. We discuss in this chapter, the history, photophysical and photochemical principles of PDT, as well as the biological effects of the photosensitizers. The main structural groups of photosensitizers are discussed and the most important drugs, either approved or in trials are described. Also, other approaches closely connected with PDT (catalytic therapy, sonodynamic therapy, photothermal therapy, and photochemical internalisation) are mentioned in this chapter. Chapter 2 - Phthalocyanine analogues containing alkyl-substituted benzenoid rings and pyridine rings are interesting compounds, because quaternation of the pyridine nitrogen is expected to form cationic amphiphilic compounds. Non peripheral long alkyl substituted zinc phthalocyanine derivatives, zinc bis(1,4- didecylbenzo)-bis(3,4-pyrido)porphyrazine and zinc bis(1,4-didecylbenzo)-bis(2,3- pyrido)porphyrazine were reacted with dimethyl sulfate and monochloroacetic acid to give their quaternary products. Also the zinc phthalocyanine derivatives reacted with diethyl sulfate to afford the sufo-substituted products. All reacted compounds showed amphiphilic character. Regio isomers of zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido)porphyrazine were also quaternized with dimethyl sulfate. Identical peaks in cyclic voltammograms appeared for these products before and after quaternization. Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido)porphyrazine was evaluated the the photo- dynamic therapy of cancer efficacy by cancer cell culture. The light exposed dimethyl sulfate quaternized zinc bis(1,4-didecylbenzo)-bis(2,3- pyrido) porphyrazines in IU-002 cells produces cell disruption that can be detected as a decrease as fluorescence. viii Arnold R. Lang Chapter 3 - The textile industry uses large amounts of water in its dyeing processes. Due to environmental problems the supercritical dyeing process has been developed. In this process supercritical carbon dioxide is used as the solvent for dyes. On the other hand, pigments, used in the formulation of paints, inks, toners and photographic emulsions can be micronized by supercritical antisolvent process. Their production in form of micrometric particles with controlled particle size distribution can largely improve their characteristics. For these reason, in the last years, supercritical fluids more and more have been proved as environmentally benign media for dyeing processes and as antisolvent to control the formation of micrometric particles. The physico-chemical properties of supercritical fluids are halfway between those of gases and liquids; more these properties can be easily modified by a simple variation of pressure or/and temperature. Therefore, supercritical fluids can be used to develop solventless or solvent reduced processes and their mass transfer properties are useful to produce micronized particles with controlled size and distribution. In this field, the publications appeared over the past years could be reviewed under two groupings, one involving the measurements of solubilities of dyes in supercritical carbon dioxide, with and without co-solvent, and supercritical CO2 dyeing of fibre, and the other involving the micronization of dyes with narrow particle size distribution using a supercritical antisolvent process. In the following, a lot of recent papers will be cited, which should give an overview of actual results on solubility and precipitation of dyes in supercritical carbon dioxide. Chapter 4 - Photochromism refers to a reversible phototransformation of a chemical species between two forms having different absorption