Literature of Chemical Technology - ACS Publications - American

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14 The Literature of Synthetic Dyes ARTHUR D. OLIN

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Toms River Chemical C o r p . , Box 71, Toms River, N. J. 08753

In more than 100 years the synthetic oped an extensive more important discovery

and valuable

periods

commercial,

quantities trivial,

dexes, PB reports, are particularly

systems.

reference

important. journals

develof

the

with the dates of difficulties

nomenclature

in the

as well as

Sources such as special

works,

abstracts,

and

A compilation

is given

in the

in-

patents

C h e m i c a l Titles

Through

journals can be determined.

books and pertinent

has

A measure

dyes. The searcher must know

and the inherent

and systematic

the main classification

leading

can be correlated

for 3300 commercial

the searchable

dye industry

literature.

the

of recent

accompanying

bibliography.

W

e know that the dye industry is over a century old, but how old is its literature? Perhaps an answer may be gleaned by examining the most important dyes that have been or are now manufactured. About 2300 of the 3300 dyes of known structure covered i n the second edition of the "Colour Index" have their dates of discovery listed. More dyes were discovered between 1890 and 1899 than i n any other decade, and before the turn of the century almost one-half of the dyes i n the index were known. Furthermore, since the 1930's and up to about the middle of the 1950's only a little more than 1 0 % of these dyes were developed. W i t h the increased competition i n recent years and with the development of specialized dyes for new fibers, there has probably been an appreciable upturn in dye discoveries, though much smaller than i n the fabulous 1890's. The most important contemporary dyes are, for the most part, of ancient vintage. W e may logically conclude that the dye industry and probably its original literature is old and has been published i n German. Basic sources, then, w i l l have to include much i n the old German journals, patents, and books. It is also likely that dye intermediates followed a similar historical development. In discussing the sources w h i c h best serve the purposes of information retrieval i n the field of dyes, we are limited to material related to the chemistry of dyes and less to their application. Several authors (3, 9) and " T h e Chemistry 254 In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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of Synthetic Dyes and Pigments," edited by H . A . L u b s , have published valuable and comprehensive bibliographies of the chemistry and application of dyes and related materials. Therefore, this discussion concentrates on the qualitative aspects of some important examples drawn from the large mass of older sources as w e l l as the more recently available information.

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Searchable

Quantities

The first step i n retrieving information is to designate searchable quantities. F o r dye intermediates a wide variety of aromatic organic compounds running the range of types such as benzene, naphthalene, anthracene, and higher polycyclic derivatives as w e l l as a host of heterocyclic materials are included. Obviously the nomenclature w i l l vary accordingly, and to this must be added the further complication of many common names, trivial names, and foreign designations. Fortunately there are ways of "decoding" these products. Thus, these trivial names are nicely related to chemical names i n Chapter 13 of " T h e Chemistry of Synthetic Dyes and Pigments." A bibliography of other dictionaries of trivial names is also included. In Volume 3 of the "Colour Index" there are an empirical formula index, through which a Chemical Abstracts (CA) name and alternate systematic and trivial names may be found, and a valuable intermediate index, where the C A names of most dye intermediates are listed w i t h their structures, molecular weights, and melting points. M a n y trivial and systematic names are cross-indexed. The indexes of C A are also extensively cross-indexed. T h e dyes themselves are often m u c h more complicated than the intermediates from w h i c h they are derived. Some dyes are mixtures while others, such as aniline and sulfur colors, are still of unknown structure. Almost all of them have a multiplicity of trade names, since many dye manufacturers make and market the same dyes. Classical, trivial, systematic, former I . G . Farbenindustrie and "Colour Index" names and numbers are known. Some C A names are useful but these are often unwieldy because of the complicated structures involved. Searchable quantities i n these cases may be any or all of these names, and it is important to determine all the synonymous designations. This can be done by inspecting C A , Patterson's " R i n g Index," and the "Glossary of Trade Names" used by the I . G . ( 8 ) . A lexicon of trivial names of organic compounds to be published by the Synthetic Organic Chemicals Manufacturing Association ( S O C M A ) and C A may shed more light on this situation. Fortunately, correlation of all trade names w i t h structure (when known) and an application name and number are possible through the "Colour Index." Starting w i t h the indexes of C A V o l . 56 all dyes were indexed by both chemical and "Colour Index" names. Searching is often done according to the classification of dyes on an application or chemical basis. M a n y methods of classification have been proposed, and though they all suffer from certain defects and overlap to a great extent,

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

256

LITERATURE

OF CHEMICAL

TECHNOLOGY

the systems employed i n the "Colour Index" are perhaps the most popular. T h e classes set up there are well defined, and each is preceded by a comprehensive explanation.

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Indexes Published jointly by the American Association of Textile Chemists and Colorists and the Society of Dyers and Colourists (England) the "Colour Index" is probably the most important reference work for the majority of chemists i n the dye field. In its four volumes and 4856 pages the structures of about 3290 dyes and a great many intermediates are given. F o r each dye this work provides information on all trade names; a special "Colour Index" ( C I ) name related to its application; a C I number to identify its structure as w e l l as syntheses or methods of manufacture; literature references; cross references to older dye indexes such as the "Colour Index," 1st edition, or Schultz's "Farbstofftabellen;" application and chemical properties; uses, and tests. The "Colour Index" also include articles on the history, development, and uniqueness of each class of dyes as w e l l as extensive bibliographies. The designations utilized find wide application, as evidenced by their use i n both Chemical Abstracts and the U . S. Tariff Report. Small supplements have been published at quarterly intervals, and a 1124-page supplement was issued i n 1963. The annual "Technical M a n u a l and Yearbook" of the American Association of Textile Chemists and Colorists is a useful supplement to the "Colour Index." It gives the trade names of American dyes and their C I names and n u m bers. I n addition, latest test methods are reported, and a valuable bibliography of current periodical and book literature indexed by subject and author is included. PB

Reports

M a n y reports and documents were obtained from Germany after W o r l d W a r II w h i c h were later published by the Publication Board ( P B ) of the Office of Technical Services whose name has since been changed to Clearinghouse for Federal Scientific and Technical Information. These reports are composed of over one-quarter million documents, a large portion of w h i c h are related to chemistry. M a n y of these were obtained by the American F I A T ( F i e l d Information Agency Technical) and British B I O S (British Intelligence Objectives Subcommittee) groups. The voluminous reports from the dye industry, captured between 1945 and 1947, contain valuable data on industrial processes of dyes and intermediates including engineering and research and development information. Because these reports were taken from the whole I . G . Farbenindustrie complex and covered many years of German preeminence i n the field, they may be considered primary, comprehensive sources.

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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Unfortunately their wealth of information is inadequately indexed and difficult to search. However, correlation indexes for the P B numbers of all B I O S and F I A T reports are available, as are page-by-page indexes for w h i c h broad subject classifications are given. A good list of the important P B reports on dyes and intermediates can be found i n Chapter 14 of " T h e Chemistry of Synthetic Dyes and Pigments." The "Bibliography of Indexes to German Chemical Products" including the I . G . Farbenindustrie Index Cards (1) may prove valuable. Most of the names used are the I . G . names and may be found in the "Colour Index." M a n y books and reference works such as the "Colour Index," "Encyclopedia of Chemical Technology," and " T h e Chemistry of Synthetic Dyes and Pigments," as w e l l as patents and journal articles, give citations to the P B reports. Frequently dye manufacturers' libraries where this information is constantly searched have developed their own extensive formula and subject indexes. Reference

Works

The best known reference work i n organic chemistry is, of course, " B e i l stein's H a n d b u c h der Organischen Chemie." It is also one of the most important sources for information on the chemistry and properties of dyes and intermediates. However, its 35-year time lag limits its usefulness, especially for the small number of dyes and intermediates w h i c h have been described i n the interim. Thus, the original fourth edition covered all organic compounds up to 1910, its first supplement extended this to 1919, and the second supplement increased the coverage through 1929. A third supplement w i l l cover the literature through 1949, but as yet no books on aromatic compounds have been issued. Besides gleaning its information from the world's literature, Beilstein gives many references to the original German patents along with their volume and page locations i n Friedlander (6). Though this work is elaborately indexed and not readily handled (up to 4877 possible classes), the subject and formula indexes are complete. E v e n complicated dyes may be found readily either by using the formula index or b y searching under their I . G . Farbenindustrie trade names i n the subject index. Another reference work of value is "Elsevier's Encyclopaedia of Organic Chemistry." This work offers the searcher the advantages of an English text and literature coverage through 1940. O n the other hand, it is m u c h less extensive than Beilstein and covers only a few parts of the field of organic chemistry. In Volume 12 there are 5700 pages on bicyclic compounds i n c l u d ing many naphthalene intermediates as w e l l as azo dyes derived from them. The patent coverage, however, is not thorough, especially for volumes p u b lished before 1951. Volume 13 covers much of the information from the journals on tricyclic condensed ring compounds, including many important anthraquinone dyes and intermediates. Volume 14, for w h i c h there are four supplements, covers tetracyclic and greater ring compounds and includes some patent references to carboxylic vat dyes and intermediates.

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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LITERATURE

OF CHEMICAL TECHNOLOGY

Abstracts

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Abstracts are among the important sources i n searching the dye literature, the foremost being Chemical Abstracts (CA). U p to 1962 Section 25 contained the specific information on dyes and textiles, but these categories have now been separated. Thus, i n 1962 dyes were covered i n section 44 and textiles i n section 48. In 1963 these sections were redesignated as 46 and'47, respectively. C A ' s remarkable indexes list dyes i n various ways, including classical names, systematic names, "Colour Index" names, and I . G . Farbenindustrie names such as Indanthrene R e d F B B or Celliton Fast Pink 4 B N . In the 1962 index of CA, V o l . 56, the "Colour Index" names are a regular entry. Crossindexing is extensive, and the formula index is complete. The German Chemisches Zentralblatt is probably a much better source of literature and patents than CA for the earlier years, especially before C A was started i n 1907. Subject indexing began i n 1889 on a semiannual basis while annual formula indexing began i n 1925. Other standard abstracts sources in English, German, and French are also useful. T h e literature of organic chemistry has been continuously abstracted since 1875. There are many fine discussions on using abstracts such as those i n Crane, Patterson, and Marr's book (2). Special abstracts are produced by some of the larger European companies i n the dye industry. Thus, there are companies whose extensive information departments regularly publish abstracts of patents a n d / o r journals relating to their special interests. A fine example of such a publication is Farbenfabriken Bayer's, Fortschrittesbericht uber neue Veroffentlichungen auf dem Gebiete der reine und angewandten Chemie (4). The section of particular value is Gruppe E , Organische Farbstoffe, as w e l l as Gruppe C . Other sources of special abstracts are some of the dye and dye application journals. The abstracts of both papers and patents under the heading, " I V . R a w Materials; Intermediates; Colouring Matters," i n the monthly Journal of the Society of Dyers and Colourists are especially valuable. Those appearing i n the American Dyestuff Reporter patent abstracts are usually related to dye application and textiles. Patents According to Crane, Patterson, and M a r r ( 2 ) , "patents are the major sources of information regarding technological advances i n chemistry." This is especially true for the dye field. Indeed, Venkataraman states i n his book that "the literature of dyestuffs is largely i n patents." Despite the academician's merited contempt for the unscientific aspects of patented information, they nevertheless represent a primary source of information on new and useful work. In searching the literature of dyes, patents frequently become the only available sources. First i n this field are the old German patents. F o r this reason the collection of German patents begun by Paul Friedlander, entitled the "Fortschritte der Teerfarbenfabrikation u n d Verwandte Industriezweige" ( 6 ) , w h i c h covers

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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the years between 1877 and 1938 i n 26 volumes, is the single most valuable source. T h e first year it covers coincides w i t h the advent of the German patent system. F e w if any prior patents by German companies w o u l d exist before this date. T h e collection carries the full text of each patent and contains subject, patent, and numerical indexes for each volume. Subject indexes are organized by classes of dyes i n each volume, and a small review of the advances during the period covered by that volume is given. However, the indexes i n each volume are sketchy and limited to such an extent that one patent expert has described Friedlander as " a monumental example of inadequate indexing." The saving grace is its accurate numerical patent index as well as the citation of corresponding foreign patents. Throughout its long history of publication, its content has changed w i t h the shift of emphasis from dyes to other synthetic organic materials. More recent coverage of German patents is found for the war years, 1939-1945, and 1950-1 i n Bayer and Stoetzer's "Deutsche Reichspatents aus dem Gebiete der Organischen Chemie." Most industrialized countries have some sort of patent laws, and for more recent work the more important patent systems must be consulted. Table I lists the classes under w h i c h dyes may be found. Several countries utilize the German patent system, and the Russians do indeed issue patents. I n general Belgian patents are good starting points for a patent search since they are issued quickly (as photostats) without prior consideration of novelty. T h e quality of the classification system varies considerably, w i t h the French being considered at the low end of the scale and the Swiss and German at the top. Reference to the patent literature may be obtained from the sources already discussed as w e l l as from journals and other patents. Recently, the international patent classification number, I . P . C . C 09 b, was assigned to dyes and intermediates. The classification system given i n Table II for U . S . dye patents shows that 7 8 % fall into Class 260—the chemistry of carbon compounds—but only 2 0 % of these are found i n readily observable subclasses while the remaining 5 8 % are scattered among many different subclasses. About 1 7 % of the patents are i n Class 8, and the only prominent subclass here is 55, accounting for only 6 % of the dye patents. These statistics (based on patents issued during the first 25 weeks of 1962) illustrate some of the problems arising from the complicated U . S . classification system. Thus, a strict chemical type may be readily searched, but the dye usage is usually not apparent. Since 1947 the references submitted i n filing each U . S . patent have been included at the end of the published patent. Journals T h e only remaining primary source is the journal literature i n w h i c h format most scientists prefer to find their information. Citations to this literature are, of course, found i n abstracts, patents, reference books, and i n the journals themselves. A relatively new source is the keyword i n context, Chem-

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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LITERATURE

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Table I.

OF CHEMICAL TECHNOLOGY

Foreign Patent Classifications for Dyes

(5)

Patent System

Classification

British French German Austrian Danish Dutch Norwegian Swedish Russian Swiss

Group I V Class X I V - 2 Class 22 Class 22 Class 22 Class 22 Class 22 Class 22 Classes 8 and 22 Class G-37

ical Titles, w h i c h was begun i n 1961. Here articles of potential interest may be quickly located i n the period of time between publication of the original article and its abstracts. T o determine and rank these contemporary journals w h i c h are important sources of articles on dyes all the issues from 6 months of Chemical Titles during 1962 were examined for the key words, dye, dyes, dyeing, dyed, and dyestuffs. A total of 166 papers of interest to workers i n the synthesis of dyes were found. Obviously there are many other articles of interest w h i c h do not have these keywords i n their titles, but the tables of contents of many of these journals show that a majority of the important articles were covered. The countries w i t h the greater numbers of leading journals are i n the order: Russia > Japan > Germany > E n g l a n d > India > Czechoslovakia = Poland = Switzerland. American journals are conspicuously absent, but some mention should at least be made of the American Dyestuff Reporter. Older lists of journals have been compiled by M e l l o n (7) and also by Crane, Patterson, and M a r r ( 2 ) , although these are based on the old CA Section 25 classification w h i c h includes textiles as well. Neither list is as comprehensive as the one provided i n the bibliography. Table II.

U . S. Patent Classes and Subclasses for Dyes % of Dyes"

Class 260 Subclass 314.5 145 279 Class 8

Chemistry, Carbon Compounds ( 7 8 % of total) Phthalocyanine H e a v y metal or A l containing azo compounds Heterocyclic 6 membered compounds w i t h one N atom-acridines

9 6 5

Bleaching and D y e i n g ; F l u i d Treatment and Chemical Modification of Textiles and Fibers ( 1 7 % of total)

Subclass 55 a

Bleaching and dyeing artificial

fibers

Based on patents issued during first 25 weeks of 1962.

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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Books

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Books are always welcome sources because their authors have already searched certain areas of the literature for us. Unfortunately, they contain little primary or original material and are quickly outdated. T h e list of books in the bibliography was developed to update the comprehensive list i n Crosland and C a d y ( 3 ) . Therefore, it is limited mainly to works on the chemistry of dyes appearing after 1952. Sources were the reviews i n the Journal of the Society of Dyers and Colourists, Chemical Abstracts (Section 2 5 ) , and L i b r a r y of Congress cards. Literature

Cited

(1) "Bibliography of Indexes to German Chemical Products," Publication IB-260, Clearinghouse for Federal Scientific and Technical Information, Springfield, Va. (2) Crane, E. J., Patterson, A. M., Marr, E. B., "A Guide to the Literature of Chemistry," John Wiley and Sons, New York, 1957. (3) Crosland, D. M., Cady, W. H., ADVAN. CHEM. SER. 10, 200 (1954). (4) Farbenfabriken Bayer, Fortschrittesberichtüberneue Veröffentlichungen auf dem Gebiete der reinen und angewandten Chemie, Leverkusen, 1914, weekly. (5) Fleischer, J., ADVAN. CHEM. SER. 4, 81 (1951). (6) Friedländer, P., Fierz-David, H. E. (eds.), "Fortschritte der Teerfarbenfabrikation und Verwandter Industriezweige," Julius Springer, Berlin, 1888-1942. (7) Mellon, M . G., "Chemical Publications," McGraw-Hill, New York, 1958. (8) Robitschek, F. O., FIAT Final Report 764, Volume 4, p. 358, Appendix 5, U. S. Department of Commerce, Washington, D. C., 1947. (9) Roosens, L., Belgische Chem. Ind. No. 12, 1293-1302 (1956).

BIBLIOGRAPHY Books, Reports,

Symposia,

and Selected

Articles

American Dyestuff Reporter, "Silver Jubilee Issue," Dec. 2, 1946. Andrews, D . B., "German Dyestuffs and Dyestuff Intermediates," 3 vols., F I A T Report 1313, Clearinghouse for Federal Scientific and Technical Information, Springfield, Va., 1949. Avery, John, "German Dyestuffs and Dyestuffs Intermediates; Azo and Lake Dyestuffs," Hobart Publishing Co., Washington, D . C , 1947. Barnett, Edward de Barry, "Coal-Tar Dyes and Intermediates," Bailliere, Tindall & Cox, L t d . , London, 1919. Batug, Frank J . , "Mixed 2-Methyl-Naphthols as Dye Intermediates," University Microfilms, Ann Arbor, 1956. Bayer, O., Stoetzer, W . , "Deutsche Reichspatente aus dem Gebiete der Organischen Chemie," Farbenfabriken Bayer, Leverkusen, 1952. Beer, John J . , "The Emergence of the German Dye Industry," (Studies in the Social Sciences, Vol. 44), University of Illinois Press, Urbana, 1959. "Beilstein's Handbuch der Organischen Chemie," 4th ed. and supplements, SpringerVerlag, Berlin, 1918. Belen'kii, L . I., "The Theory of Dyeing, an Attempt at Its Practical Application," Gizlegprom, Moscow, 1958. Bentley, K. W . , "The Chemistry of Natural Products, V o l . I V , The Natural Pigments," Interscience Publishers, New York and London, 1960. Bernard, Walter, "Bleichen und Farben von Textilien," Fachverlag Schiele and Schon G m b H , Berlin, 1959. Bird, C. L . , "The Theory and Practice of Wool Dyeing," Society of Dyers and Colourists, Bradford, England, 1947.

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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Blackshaw, H . , Brightman, R., "Dictionary of Dyeing and Textile Printing," George Newnes, L t d . , London, 1961. Boardman, G. L . , /. Soc. Dyers Colourists 66, 397-405 (1950). Bogoslovskii, B. M . , Laptev, N . G., "Khimiya krasitelei. Uchebnik dlya khimicheskikh atdelenil tekstil nykh tekhnikumov (Chemistry of Dyes—Text Book for Chemical Departments of Textile Technical Schools)," Rossiiskoe Tekh. Izdatel., Moscow, 1960. Bogoslovskii, B. M . , Laptev, N . G., "Khimiya krasitelei (Chemistry of Dyes)," Gosudarstvennoe Nauchno-tekhnicheskoe Izdatel'stvo Literatury po Legkoi Promyshlennosti, Moscow, 1957. Bradley, W., "Recent Progress in the Chemistry of Dyes and Pigments," Lectures, Monographs, and Reports 1958, No. 5, Royal Institute of Chemistry, London. Cain, J . C , "The Manufacture of Dyes," The Macmillan Co., Ltd., London, 1922. Cain, J . C , "The Manufacture of Intermediate Products for Dyes," 2nd ed., The Macmillan Co., Ltd., London, 1919. Cain, J . C , Thorpe, J . F., "The Synthetic Dyestuffs and the Intermediate Products from Which They Are Derived," Griffin & Co., Ltd., London, 1933. Caspar, E. C , /. Soc. Dyers Colourists 66, 177-181 (1950). Chekalin, M . A., "Khimiya i tekhnologiya organicheskikh krasitelei (Chemistry and Technology of Organic Dyes)," Gosudarstvennoe Nauchno-tekhnicheskoe Izdatel'stvo Khimicheskoi Literatury, Moscow, 1956. Chekalin, M . A., Eremin, F. F., "Proizvodstvo Azokrasitelei (Manufacture of Azo Dyes)," Gosudarstvennoe Nauchno-tekhnicheskoe Izdatel'stvo Khimicheskoi Literatury, Moscow and Leningrad, 1952. Clayton, Ellis, "Identification of Dyes on Textile Fibres and Detection of Metals in Fibrous Materials, Dyes, and Organic Pigments," 2nd ed., Society of Dyers and Colourists, Bradford, England, 1946. Cockett, S. R., Hilton, K. A., "Basic Chemistry of Textile Colouring and Finishing," National Trade Press, L t d . , London, 1955. Cockett, S. R., Hilton, K. A., "The Dyeing of Cellulose Fibres and Related Processes," Leonard Hill, L t d . , London, 1961. "Colour Index," published jointly by American Association of Textile Chemists and Colorists, and Society of Dyers and Colourists (England), Lowell, Mass., 2nd ed., 1956; supplement, 1963. Cox, J . H . , " A n Evaluation of Carriers for Use in the Application of Acid Dyestuffs to Dynel," Masters Thesis, Georgia Institute of Technology, Atlanta, 1952. Curtis, C. A., "Artificial Organic Pigments and Their Applications," transl. by E . Fyleman, I. Pitman & Sons, Ltd., London, 1930. Czechoslovakia Ministerstve Spotrebniho Prumyslu, "Veda a Vyzkum v Prumylsu Textilnim Sbornik Predasek z I Kolloresleckeho Sjegdu v Tatranske' Lomnici 1957," Prague, 1958. Davidson, A., "Intermediates for Dyestuffs," Ernest Benn, L t d . , London, 1926. Derret-Smith, D., Gray, J . , "The Identification of Vat Dyes on Cellulosic Materials," Pergamon Press, Ltd., Oxford, 1967. Diserens, Ludwig, "Neueste Fortschritte und Verfahren in der chemischen Technologie der Textilfasern,": Part I (French, German, English eds.): "Progres realises dans l'application des matieres colorantes," 2 me., rev. et mise a jour., Editions Teintex, Paris, 1950," "Die neuesten Fortschritte in der Anwendung der Farbstoffe; Hilfsmittel in der Textil-Industrie," 3 vols., Neubearb. und verm. 2 Aufl., Birkhauser Verlag, Basel, 1946-1949. "The Chemical Technology of Dyeing and Printing," transl. and rev. from 2nd German ed. by Paul Wengraf and Herman P. Bauman, Reinhold Publishing Corp., New York, 1948-1951. Part II (German ed. only): "Neue Verfahren in der Technik der Chemischen Veredlung der Textilfasern," 2 vols., Birkhauser Verlag, Basel, 1946-1949. Donaldson, Norman, "The Chemistry and Technology of Naphthalene Compounds," Edward Arnold, L t d . , London, 1958. Fierz-David, Hans Eduard, "Grundlegende Operationen der Farbenchemie von Hans Eduard Fierz-David and Louis Blangey," Springer-Verlag, Wien, 1952.

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.

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Synthetic

Dyes

Fierz-David, H . E., "Kunstliche organische Farbstoffe," Springer-Verlag, Berlin, 1935. Fierz-David, H . E., Blangey, L . , "Fundamental Processes of Dye Chemistry," transl. from 5th Austrian ed. by Paul W . Vittum, Interscience Publishers, New York, 1949. Fierz-David, H . E., Blangey, L . , "Grundlegene Operationen der Farben-Chemie," 7. unveranderte Aufl., Springer-Verlag, Wien, 1947. "Final Report on the Census of Production for 1945," Vol. 2, Trade 3, Dyes and Dyestuffs, H.M.S.O., London, 1952. Foerst, W., Jung, W., eds., "Internationales Farbensymposium, 2., Schloss Elmau, 1964," Verlag Chemie, 1966. "The Food and Color Additives Directory," Hazleton Laboratories Inc., Falls Church, Va., 1961. "Food Standards Committee Report on Colouring Matters," Ministry of Foods, H.M.S.O., York House, Kingsway, London W C 2 , England, 1954. Fort, M . , Lloyd, L . L . , "The Chemistry of Dyestuffs; A Manual for Students of Chemistry and Dyeing," University Press, Cambridge, England, 1950. Fox, M . R., "Vat Dyestuffs and Vat Dyeing," John Wiley & Sons, New York, 1947. Frank, G. H . , "The Manufacture of Intermediates and Dyes; An Introduction to Works Practice," Chemical Publishing Co., New York, 1952. Georgievics, G. C. T. von, Grandmougin, E . , " A Text-book of Dye Chemistry; The Chemistry of Dyestuffs," transl. and rev. from 4th German ed. (with additions) by F. A . Mason, Scott, Greenwood, Ltd., London, 1920. Gerstner, H . , "Das Verhalten der direktziehenden Farbstoffe gegen tierische Fasern, Cellulose-und Kunstspinnfasern," Akademie-Verlag, Berlin, 1957. Gerstner, H . , "Die Chemie der Applikation von Komplexfarbstoffen," AkademieVerlag, Berlin, 1959. Gore, T. S. et ah, eds., "Recent Progress in the Chemistry of Natural and Synthetic Colouring Matters and Related Fields," Academic Press, New York and London, 1962. Green, A . G., "The Analysis of Dyestuffs and Their Identification in Dyed and Coloured Materials," 3rd ed., J . B. Lippincott Co., Philadelphia, 1920; reprinted by Griffin & Co., L t d . , London, 1949. Haller, R., "Der Colorist Eine Monographic des Textilchemikers," Verlag Melliand Textilberichte, 2nd ed., Heidelberg, 1953. Hamer, Frances M . , "The Cyanine Dyes and Related Compounds," Interscience Publishers, New York, 1964. Harrison, A. W . C , "The Manufacture of Lakes and Precipitated Pigments," 2nd ed., Leonard H i l l , Ltd., London, 1957. Heerman, Paul, "Farberei-und textilchemische Untersuchungen; Anleitung zur chemischen und koloristischen Untersuchung und Bewertung der Rohstoffe, Hilfsmittel und Erzeugnisse der Textilveredlungsindustrie," Springer-Verlag, Berlin, 1956. Hewitt, J . T., "Synthetic Colouring Matters; Dyestuffs Derived from Pyridine, Quinoline, Acridine, and Xanthene," Longmans, Green, & Co., London and New York, 1922. Hollerer, Hanns Erich, "Uber zwei-und mehrkernige Pyrrylpolymethinfarbstoffe," Munchen, Germany, 1959. Hopf, H . , "Kunstliche Organische Farbstoffe, Band I Allgemeines, Grundlegende Operationen, Wichtige Zwischenprodukte, Band II Die wichtigsten Farbstoffe, ihre Herstellung und hauptsachlichen Eigenschaften," Verlag der Chemiestudierenden an der Eidgenossischen Technischen Hochschule, Zurich, 1956. Horsfall, R. S., Lawrie, L . G., "The Dyeing of Textile Fibres," 2nd ed., Chapman & Hall, L t d . , London, 1949. Izrael'son, B. I., Ratnovskaya, Ya. D., "Kubovye krasiteli dlya tekstil'noi promyshlennosti (Vat Dyes for the Textile Industry)," A . L . Byal'skii, ed., Tsental Byuro, Moscow. Josephy, E . , Radt, F., eds., "Elsevier's Encyclopaedia of Organic Chemistry," Elsevier Publishing Company, Amsterdam, 1940. "Jubilee Volume," Society of Dyers and Colourists, Bradford, England, 1934. Khimiko, "Analiticheskir kontrol v kozhevennom i dubirnoekstraktovom proizvodstve. (Chemical-Analytical Control in the Leather and Dye Extracting Industry—part 2 ) " Gizlegprom, 1955. Kierstead, S. P., "Natural Dyes," Bruce Humphries, Boston, 1950. ((

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LITERATURE

OF CHEMICAL TECHNOLOGY

Kirk, R. E . , Othmer, D. F., eds., "Encyclopedia of Chemical Technology," 2nd edition, Interscience Publishers, New York, 1963 (sections on anthraquinone, azine, and azo dyes; color and constitution of organic dyes; cyanine dyes; dyes and dye intermediates; dyes, reactive indigoid and natural dyes; and dyes—application and evaluation). Kirrmann, A., et al. "Traite de chimie organique T. X I X Pyrrole et Composes pyrroliques, pigments tetrapyrroliques, Noyaux pyrroliques complexes indigo et colorants indigoides," Masson et Cie, Paris, 1954. Kittel, H . , ed., "Wagner's Taschenbuch der Farben und Werkstoffkunde," Wissensch. Verlag, Stuttgart, 1953. Kittel, H . , ed., "Pigmente: Herstellung, Eigenschaften, Anwendung," Wissenschaftliche Verlagegesellschaft G m b H , Stuttgart, 1960. Kogan', Josif M . , "Khimiya krasitelei (Chemistry of Dyes)," 3rd ed., Gosudarst. Nauch.-Tekh. Izdatel. Khim. L i t . , Moscow, 1956. Lastovskii, R. P., Vainshtein, Yu. I., "Teknicheskii analiz v proizvodstve promezhutochnykh produktov i krasitelei" (Technical Analysis in the Manufacture of Intermediate Products and Dyes), 3rd ed., Gosudarst. Nauch. Techl. Izdatel. Khim. Lit., Moscow, 1958. Leggett, W . F., "Ancient and Medieval Dyes," Chemical Publishing Co., New York, 1944. L i u , Ching-i, "The Structure and Properties of Some Metallic Derivatives of Dyes," University of Illinois Press, Urbana, 1951. Lubs, H . A., ed., "The Chemistry of Synthetic Dyes and Pigments, Reinhold Publishing Corp., New York, 1955. Mecheets, D., ed., "Veredler Jahrbuch Deutscher Farber-Kalender," Franz Eder Verlag, Munich, 1951 (annual). Meier, Hans, "Die Photochemie der Organischen Farbstoffe," Springer-Verlag, Berlin, 1963. Melzer, G., "Handbuch fiir die textile Nassveredlung," V E B Verlag Technik, Berlin, 1956. "Methods for the Analysis of Water-Soluble Coal-Tar Dyes Permitted for Use in Foods," British Standards Institution, London, 1960. Moser, F. H . , Thomas, A. L . , "Phthalocyanine Compounds," Reinhold Publishing Corp., New York, 1963. Myasnikov, A. A., "Sernistye vodorastvorimye krasiteli (Water-Soluble Sulfur Dyes)," Gosudarst. Nauch.-Tekh. Komitet Sovet. Ministrov SSSR, Moscow, 1960. Nagai, Y., Kato, S., eds., "The Selected Papers of Dr. Toshio Maki on Vat Dyes," University of Tokyo, 1955. Nitschke, G., "Chemische Technologie und Praxis der Farberei Band I, Die Farbstoffe und das Farben der Wolle," V E B Verlag Technik, Berlin, 1958. Olney, L . A., "Textile Chemistry and Dyeing," 10th ed., Spaulding-Moss Co., Boston, 1947. Patterson, A . M . , Capell, L . T., Walker, D., "The Ring Index," 2nd ed., American Chemical Society, Washington, D. C , 1959. Perkin, A. G., Everest, A. E . , "Natural Organic Coloring Matters," Longmans, Green, & Co., New York, 1918. "Perkin Centenary London, 100 Years of Synthetic Dyestuffs," Pergamon Press L t d . , London, 1958. Phadke, B. N . , "History of Dyes and Dyeing in the Bombay Presidency," Dastane Brothers Home Service Ltd.,, Poona, 1947. "The Physical Chemistry of Dyeing and Tanning," Discussions Faraday Soc. 16 (1954). Poray-Koshits, A . E . , "Izbrannye Trudy, Raboty v Oblasti Organicheskoy Khim., Khim Krasyashchikh Veshclestv i Terii Krashiniya (Selected Works. Work in Organic Chemistry, The Chemistry of Coloring Matters, and the Theory of Dyeing)," Akademiya Nauk SSSR., Moscow and Leningrad, 1949. Pratt, L . S., "The Chemistry and Physics of Organic Pigments," John Wiley & Sons, New York, 1947. "Problemes Nouveaux en Teinture, Impression, Blanchiment, Appretage," Institut Textile de France, Paris, 1960. Rawson, C , Gardner, W . M . , Laycock, W . F., " A Dictionary of Dyes, Mordants, and Other Compounds Used in Dyeing and Calico Printing," Griffin & Co., L t d . , London, 1937.

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