Analytical Chemistry of Synthetic Colorants

222 Pages·1995·4.34 MB·English

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

Analytical Chemistry of Synthetic Colorants
Advances in Color Chemistry Series - Volume 2
Analytical Chemistry of Synthetic
Colorants
edited by
A.T. PETERS
Chemistry & Chemical Technology,
University of Bradford,
Bradford
UK
and
H.S. FREEMAN
Dept. of Textile Engineering, Chemistry & Science,
North Carolina State University,
Raleigh
USA
SPRINGER SCIENCE+BUSINESS MEDIA, LLC
© 1995 Springer Science+Business Media New York
Originally published by Chapman & Hali in 1995
Softcover reprint of the hardcover 1s t edition 1995
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Library of Congress Catalog Card N umber: 94-71949
ISBN 978-94-010-4593-3 ISBN 978-94-011-1358-8 (eBook)
DOI 10.1007/978-94-011-1358-8
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Preface
More than one and a half decades have passed since the last book was
published describing developments in the analytical chemistry of synthetic
colorants. In the intervening period, the scope and technical capabilities of
instrumentation for analysing dyes and pigments has significantly expanded.
It is now possible to rapidly resolve a number of problems whose solutions
were previously either unattainable or very difficult to achieve. For instance,
the unambiguous assignment of all the signals in the proton NMR spectrum
of a trisazo direct dye, and the confirmation of the molecular weight of
involatile, and, in particular, sulphonated dyes, without derivatisation, are
now routine analytical techniques in many laboratories today. In addition,
it is now possible to record the NMR spectrum of a dye molecule on less
than 1 mg of material, and we are no longer limited to solution spectra,
since solid samples can now be routinely analysed in NMR experiments.
Whilst not attempting to be all encompassing, this volume is intended to
bridge the gap between what was covered in the earlier work edited by
Professor Venkataraman and the developments which have since ensued in
some key areas. It provides important updates in X-ray crystallography,
proton NMR, IR spectroscopy and mass spectrometry, and additionally
covers topics such as ESR, micro spectrophotometry and emission spectroscopy.
The X-ray chapter provides a critical analysis of reports of new crystal
forms of various organic pigments and summarises some of the hazards
connected with the characterisation of a proposed new form. The NMR
chapter contains a review of the fundamental principles of solid state NMR
and some examples of the types of problems which can be solved using this
technique. The IR chapter focuses on the use of MO techniques to predict
the NIR spectrum of a dye molecule not yet synthesised, and includes
specific examples of dyes useful for laser printers, optical recording media,
and other non-textile areas. The chapters on ESR and'microspectro-
photometry cover, amongst other matters, the utility of these analytical
tools in characterising the diffusion, distribution, and molecular environment
of dyes in a polymer matrix. A further chapter illustrates the application of
emission spectroscopy to the evaluation of optical brightening agents.
The editors noted in their Preface to the first volume of this series that
colour chemistry was very much alive, and expanding into realms totally
unenvisaged in the not too distant past. This new volume exemplifies the
concurrent developments which have taken place in analytical techniques
and structural characterisation. It contains a blend of fundamental concepts
VI PREFACE
and practical applications germane to the topics covered, thus rendering it
of interest to scientists involved in teaching and research areas and to
practising analytical chemists interested in organic colorants.
The editors wish to thank all the contributors to the various chapters;
without their expertise and commitment, this volume would not have become
a reality.
A.T.P.
H.S.F.
Contributors
R.D. Bereman North Carolina State University, Department of
Chemistry, Box 8204, Raleigh, NC 27695, USA
M. DaRocha Sun Chemical Corporation, 441 Tompkins Avenue,
Rosebank, Staten Island, NY 10305, USA
U.S. Freeman North Carolina State University, Department of Textile
Engineering, Chemistry and Science, College of Textiles,
Box 8301, Raleigh, NC 27695, USA
K.P. Ghiggino University of Melbourne, Department of Physical
Chemistry, Victoria 3052, Australia
J. Jirman Research Institute of Organic Syntheses, 532 18
Pardubice-Rybitvi, Czech Republic
Y.K. Kamath Textile Research Institute, PO Box 625, Princeton, NJ
08542, USA
A. Lycka Research Institute df Organic Syntheses, 532 18,
Pardubice-Rybitvi, Czech Republic
M. Matsuoka Kyoto Women's University, 35 Kitahiyoshi
Imakumano, Higashiyama-ku, Kyoto 605, Japan
C. Nicolaou Sun Chemical Corporation, 441 Tompkins Avenue,
Rosebank, Staten Island, NY 10305, USA
A.T. Peters Reader in Colour Chemistry, Chemistry & Chemical
Technology, University of Bradford, Bradford, West
Yorkshire BD7 IDP, UK
S.B. Reutsch Textile Research Institute, PO Box 625, Princeton, NJ
10502, USA
J. Straka Institute of Macromolecular Chemistry, Czechoslovak
Academy of Sciences, 16206 Prague, Czech Republic
R.B. Van Breemen University of Illinois at Chicago, Dept. of Medicinal
Chemistry and Pharmocognosy, College of Pharmacy,
833 South Wood Street, Chicago, IL 60612-7273, USA
Vlll CONTRIBUTORS
H.-D. Weigmann Textile Research Institute, PO Box 625, Princeton, NJ
08542, USA
A. Whitaker Brunei University, Department of Physics, Uxbridge,
Middlesex UB8 3PH, UK
Contents
1 X-ray powder diffraction of synthetic organic colorants 1
A. WHITAKER
1.1 Introduction I
1.1.1 Diffraction of X-rays from crystals I
1.1.2 Advantages and disadvantages of the powder technique 2
1.1.3 Reliability of an X-ray pattern 4
1.1.4 Presentation of X-ray powder data 5
1.2 X-ray powder diffraction data 5
1.2.1 Nitroso and nitro compounds 6
1.2.2 Monoazo compounds 6
1.2.3 Disazo compounds 19
1.2.4 Azoic compounds 22
1.2.5 Stilbene optical brighteners 22
1.2.6 Quinacridones 24
1.2.7 Dioxazines 27
1.2.8 Amino ketone compounds 28
1.2.9 Anthraquinone compounds 28
1.2.10 Perylene compounds 31
1.2.11 Indigoids 32
1.2.12 Phthalocyanines 32
1.2.13 Miscellaneous compounds 38
Acknowledgement 40
References 40
2 Solid state NMR spectroscopy of synthetic dyes 49
A. LYCKA, J. JIRMAN and J. STRAKA
2.1 Introduction 49
2.2 Basic principles of cross polarization/magic angle spinning measurements 50
2.2.1 Dipolar interactions 50
2.2.2 Chemical shift anisotropy 52
2.2.3 Cross polarization 53
2.2.4 Cross-polarization/magic angle spinning method 55
2.3 Examples of solid state NMR spectra of dyes 56
2.4 Survey of published chemical shift data on the solid state 66
2.4.1 "C NMR data 66
2.4.2 I5N NMR data 72
2.5 Conclusions 73
Acknowledgement 73
References 74
3 Near IR spectroscopy 75
M. MATSUOKA
3.1 Introduction 75
3.2 Chromophoric systems ofNIR dyes 76
3.2.1 Intramolecular charge-transfer chromophores 77
x CONTENTS
3.3 NIR spectra of dyes 78
3.3.1 Cyanine dyes 79
3.3.2 Quinone dyes 85
3.3.3 Metal complex dyes 87
3.3.4 Phthalocyanine and naphthalocyanine dyes 89
3.3.5 Azo dyes 91
3.3.6 Miscellaneous chromophoric systems 92
3.4 Conclusion 94
References 94
4 Mass spectroscopy 96
R.B. VAN BREEMEN
4.1 Introduction 96
4.2 Ionization methods 98
4.2.1 Electron impact 98
4.2.2 Chemical ionization 99
4.2.3 Desorption EI and CI 100
4.2.4 Field desorption 102
4.2.5 Fast atom bombardment and liquid secondary ion mass spectrometry 103
4.2.6 Laser desorption 107
4.2.7 Plasma desorption 108
4.2.8 Thermospray 110
4.2.9 Electrospray and ion spray 112
4.3 Conclusion 114
References 115
5 Electron spin resonance spectroscopy 117
H.S. FREEMAN and R.D. BEREMAN
5.1 Introduction 117
5.2 Basic principles 117
5.2.1 Spin relaxation and line broadening 118
5.2.2 The g-value 120
5.2.3 Hyperfine coupling 120
5.2.4 Anisotropic effects 121
5.3 Applications 122
5.3.1 Sensitizing and desensitizing dyes 122
5.3.2 Azo dyes 124
5.3.3 Triarylmethane dyes 125
5.3.4 Acridine dyes 126
5.3.5 Miscellaneous dyes 127
5.4 Conclusion 131
References 132
6 Microspectrophotometry 133
H.-D. WEIGMANN, Y.K. KAMATH and S.B. RUETSCH
6.1 Introduction 133
6.2 Microdensitometry and microspectrophotometry 133
6.2.1 Instrumentation 133
6.2.2 Analysis of in situ dye spectra 135
6.2.3 Dye concentration profiles in fibres and films 137
6.2.4 Applications 144
6.3 Microfluorometry 156
6.3.1 Background 156
6.3.2 Methods of measurement 159
CONTENTS xi
6.3.3 Applications 162
6.4 Conclusion 168
References 168
7 Emission spectroscopy 171
K.P. GHIGGINO
7.1 Introduction 171
7.2 Principles 171
7.3 Techniques 175
7.3.1 Steady state measurements 175
7.3.2 Time-resolved measurements 178
7.4 Applications to fluorescent whitening 'dyes' 181
Acknowledgements 184
References 185
8 Identification and analysis of diarylide pigments by spectroscopic
and chemical methods 186
C. NICOLAOU and M. DA ROCHA
8.1 Introduction 186
8.1.1 Historical background 186
8.1.2 Method of manufacture 187
8.2 Analytical methodology of diarylide pigments 189
8.3 Analysis of diarylide pigments by infra-red spectroscopy 192
8.3.1 Sample preparation 192
8.3.2 Characteristic bands of the IR spectra of diarylide pigments 193
8.4 Analysis of diarylide pigments by visible spectroscopy 195
8.5 Thin layer chromatography in diarylide pigments 197
8.5.1 Identification of diarylide pigments 198
8.5.2 Determination ofunreacted coupler in diarylide pigments 199
8.5.3 Determination of aromatic amines in diary Ii de pigments 199
8.5.4 Analysis offatty diamines and triamines in diarylide pigments 200
8.6 General scheme for the analysis in diarylide pigments 200
8.7 Identification of diarylide pigments by reduction 204
8.8 High performance liquid chromatography of aromatic amines
in diarylide pigments 204
8.8.1 Determination of 3,3' -dichlorobenzidine in diarylide pigments 205
8.8,2 Determination of 2,5-dimethoxy-4-chloroaniline (DMCA) in
c.1. Pigment Yellow 83 205
8.9 Gas chromatography of 3,3' -dichlorobiphenyl in diarylide pigments 206
Acknowledgements 207
References 207
Index 208