Modern Colorants: Synthesis and Structure

255 Pages·1995·18.277 MB·English

by  A. T. Peters, H. S. Freeman (eds.)

Modern Colorants: Synthesis and Structure
Advances in Color Chemistry Series - Volume 3
Modern Colorants:
Synthesis and Structure
Edited by
A. T.PETERS
Chemistry and Chemical Technology
University of Bradford
UK
and
H. S. FREEMAN
Department of Textile Engineering, Chemistry & Science
North Carolina State University
Raleigh
USA
Springer Science+Business Media, LLC
First edition 1995
© 1995 Springer Science+Business Media New York
Originally published by Chapman & Hali in 1995
Softcover reprint of the hardcover lst edition 1995
Typeset in 1O/12pt Times by Columns, Reading, Berkshire
ISBN 978-94-010-4592-6 ISBN 978-94-011-1356-4 (eBook)
DOI 10.1007/978-94-011-1356-4
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Preface
Although the research actIvItIes of dyestuff chemists worldwide have been
influenced to a great extent, in recent years, by the need to respond to a variety
of environmental issues associated with the manufacture and application of
synthetic dyes and pigments, a significant level of targeted research continues to
be devoted to new chemistry aimed at enhancing the technical properties of dyes
in commerce. This book is a presentation of various aspects of basic research
conducted during the past decade but not reported in the recent review literature.
The coverage herein is unique in that it emphasizes systematic approaches
commonly utilized in the design and synthesis of dyes and pigments and the
required intermediates.
While it is well known that certain transition metals are important in the
synthesis of technically viable metallized dyes for polyamide and protein fibers,
these metals are demonstrated in Chapter 1 also to be effective agents in the
regiospecific placement of substituents into azo compounds. The scope and
limitations of this chemistry are presented. In other synthetic work, a description
of the different processes employed to produce the major families of reactive
dyes is presented. In Chapter 4, special attention is given to reactive dyes
containing more than one reactive group, and to the more recent developments
in the field. The two chapters which follow provide a review of the recent
literature pertaining to novel chromophores and dyes for the D2T2 process,
respectively. The former covers the main classes of colorants utilized in a
variety of applications, and the latter reports the variety of structural types
developed to afford improved D2T2 dyes. The chemistry of organic pigments is
presented and includes details pertaining to the production and properties of the
desirable physical forms of the major pigment classes. The book also engages
the reader with a discussion of theoretical concepts important in dyestuff
chemistry. The chapters pertaining to NIR dyes and computer-assisted dyestuff
design describe the utility of quantum chemical methods in the design and
synthesis of organic dyes, and are written with examples illustrating the
advantages of such an approach. The direction of future developments in this
important area is also presented. A chapter covering amphiphilic dyes provides a
review of the properties and commercial potential of colorants containing a
built-in surfactant moiety. The principles associated with the unique properties
of the resulting molecules are also presented.
It is envisioned that this volume, which reflects the expertise of leaders in the
field of colour chemistry, will prove useful to academic and industrial scientists
seeking a central source of fundamental and practical information pertaining to
vi MODERN COLORANTS
the syntheses and structures of modem organic colorants. In this regard, the
editors acknowledge, with appreciation, the contribution of the authors of each
chapter.
A.T.P.
R.S.F.
Contributors
E. Barni Dipartimento di Chimica Generale ed Organica
Applicata, Universita degli Studi di Torino, Corso M.
D'Azeglio n. 48,10125 Torino, Italy
R. Bradbury Zeneca Specialties, PO Box 42, Hexagon House,
Blackley, Manchester M9 8ZS, UK
K. Carr Zeneca Specialties, PO Box 42, Hexagon House,
Blackley, Manchester M9 8ZS, UK
A. P. Chorlton Zeneca Specialties, PO Box 42, Hexagon House,
Blackley, Manchester M9 8ZS, UK
W. S. Czajkowski Institute of Dyes, Technical University of -Lodz, ul.
Zwirki 36, 90-924-Lodz, Poland
H. S. Freeman Department of Textile Engineering, Chemistry and
Science, North Carolina State University, Raleigh,
North Carolina 27695, USA
J. Griffiths Department of Colour Chemistry and Dyeing,
University of Leeds, Leeds LS2 9JT, UK
A. J. Klaus Chemical Engineering and Industrial Chemistry
Laboratory, Swiss Federal Institute of Technology,
Zurich (ETH), CH 8092 Zurich, Switzerland
R. Naef Department of Textile Dyes, Ciba-Geigy Ltd., Basle,
Switzerland
A. T. Peters Chemistry and Chemical Technology, Department of
Chemical Engineering, University of Bradford,
Bradford, West Yorkshire BD7 1DP, UK
P. Savarino Dipartimento di Chimica Generale ed Organica
Applicata, UniversWt degli Studi di Torino, Corsa M.
D' Azeglio nA8, 10125 Torino, Italy
G. Viscardi Dipartimento di Chimica Generale ed Organic a
Applicata, Universita degli Studi di Torino, Corso M.
D' Azeglio nA8, 10125 Torino, Italy
Contents
1 Transition metals in dye synthesis 1
A. J. KLAUS
1.1 Introduction 1
1.2 The principle of cyclometallation 2
1.3 Syntheses of metallacycles 4
1.3.1 Direct cyclometallation 4
1.3.2 Transmetallation 9
1.3.3 Ligand exchange 9
1.4 Cleavage of the metal--carbon a-bond: preparative applications 11
1.4.1 Halogenations 11
1.4.2 Reactions with hydroxide, alkoxides and aryloxides 13
1.4.3 Reactions with alkynes . 15
1.4.4 Reactions with alkenes or alkenones 16
1.4.5 Reactions with C=O 16
1.4.6 Reactions with isonitriles 20
1.4.7 Reactions with cyanide 22
1.4.8 Reactions with thiocyanogen 22
1.4.9 Reactions with sodium amide 23
1.4.10 Reactions with nitric acid 23
1.4.11 Reactions with organo-tin compounds 24
1.4.12 Reactions with organo-lithium compounds or Grignard reagents 24
1.4.13 Reactions with alkyl halides 25
1.4.14 Reactions with acyl halides 26
1.5 Miscellaneous reactions 27
1.5.1 Introduction of a carboxyl group 27
1.5.2 Introduction of a sulfonic acid group 28
1.5.3 Oxidation of cyciopaUadated compounds: synthesis of naphthols and
naphthoquinones 29
1.5.4 Synthesis of ortho, ortho-dihalogenated anilines 29
1.6 Catalytic reactions 32
1.7 Amino-indazoles: precursors for diazonium and coupling components 34
1.8 Conclusions 34
Acknowledgements 35
References 36
2 Approaches to the design and synthesis of near-infrared
absorbing dyes 40
J. GRIFFITHS
2.1 Introduction 40
2.2 General approaches to infrared-absorbing systems 41
2.3 Cyanine-type chromophores 44
2.3.1 Increasing the length of the conjugating bridge 45
2.3.2 Increasing the effective electron-donor strength of terminal heterocyclic residues 47
2.3.3 Modification ofthe conjugating bridge 47
2.4 Donor-acceptor chromophores 50
2.4.1 Increasing the length of the conjugating bridge 51
x MODERN COLORANTS
2.4.2 Increasing the electron-donating strength of the donor 52
2.4.3 Increasing the electron-withdrawing strength of the acceptor 54
2.4.4 Modification within the conjugating bridge 54
2.4.5 Some examples of the design of infrared donor - acceptor systems 55
2.5 Conclusions 61
References 61
3 Organic pigments 63
w. S. CZAJKOWSKI
3.1 Introduction 63
3.2 Azo pigments and lakes 65
3.2.1 Azo pigments 65
3.2.2 Azo lakes 71
3.3 Phthalocyanines 76
3.4 Carbocyclic pigments 77
3.5 Heterocyclic pigments 78
3.5.1 Isoindolines 78
3.5.2 Perylenes 79
3.5.3 Quinacridones 80
3.5.4 Diketopyrrolo-pyrroles 80
3.5.5 Other heterocycles 82
Acknow ledgements 84
References 84
4 Reactive dyes, especially bireactive molecules: structure and
synthesis 87
K.CARR
4.1 Introduction 87
4.2 Monofunctional and homo bi-or polyfunctional dyes 89
4.2.1 Fluorochloropyrimidines 89
4.2.2 Phosphonic acid dyes 91
4.2.3 Bis-monochlorotriazine dyes 92
4.2.4 Monofluorotriazinyl dyes 97
4.2.5 Dyes containing quaternary ammonium groups 98
4.2.6 Mono-and polyvinylsulphonyl dyes 102
4.3 Hetero bi-or polyfunctional dyes 106
4.3.1 Vinyl sulphonelhalotriazine dyes 106
4.4 Conclusions 119
References 121
5 Novel chromophores 123
A. P. CHORLTON
5.1 Introduction 123
5.2 Pigments 124
5.2.1 Di-keto-pyrrolopyrroles 124
5.2.2 Isoindolines 126
5.2.3 Quinacridones 129
5.2.4 Annulenes 130
5.2.5 Aza polycyclics 132
5.3 Dyestuffs 134
5.3.1 I, I-Dicyanobutadienes 134
5.3.2 Quinodimethanes 136
CONTENTS Xl
5.3.3 Triphenodioxazines and related iminodimethanes 139
5.3.4 Miscellaneous chromophores 141
5.4 High technology applications 144
5.4.1 Dithiolenes and related compounds 144
5.4.2 Squariliums and croconiums 145
5.4.3 Quinones 146
5.4.4 Miscellaneous chromophores 147
5.4.5 Novel chromophores from natural products 148
5.5 Future trends 150
References 150
6 Dyes for dye diffusion thermal transfer (D2T2) printing 154
R.BRADBURY
6.1 Introduction 154
6.2 Properties required of D2T2 dyes 155
6.3 Major dye classes evaluated for use as D2T2 dyes 156
6.3.1 Anthraquinone dyes 156
6.3.2 Azo dyes 159
6.3.3 Methines 166
6.3.4 Azamethines 170
6.3.5 Merocyanines 173
6.3.6 Quinophthalones 174
6.4 Conclusions 175
References 175
7 Amphiphilic dyes 177
E. BARNI, P. SAVARINO and G. VISCARDI
7.1 Introduction 177
7.2 Amphiphilic dyes in Langmuir-Blodgett films 180
7.3 Synthetic bilayers membranes 190
7.4 Interactions of amphiphilic dyes with organized assemblies 194
7.5 Photographic processes 197
7.6 Dyeing processes 198
7.7 Analytical and environmental applications 200
7.8 Conclusions 202
References 203
Appendix 204
8 Computer-assisted dyestuff design and synthesis 213
R.NAEF
8.1 Introduction 213
8.2 Quantum-theoretical methods: Scope and limitations 214
8.2.1 HMO method 214
8.2.2 Semiempirical SCF-CI methods 216
8.3 Examples 217
8.3.1 Dichroic dyes for liquid crystals 217
8.3.2 Fluorescent dyes 220
8.3.3 Halochromic dyes 220
8.3.4 Near-infrared dyes 223
8.3.5 Sensitizing dyes 227
8.3.6 Solvatochromism 228
8.3.7 Tautomerism 230
xii MODERN COLORANTS
8.4 Synthetic aspects 232
8.5 Future developments 236
References 238
Index 241