Manufacture of Dyes and A l l i e d Products1 M. L. CROSSLEY Calco Chemical Division, American Cyanamid C o . , Bound Brook, N . J .
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H E manufacture of dyes and allied products is a complicated business. I t s success is dependent upon a thorough and efficient integration of several types of human capacity for service and the inspirational leadership which can weld them into one composite, affective, productive force. Science, art, technology, finance, business, and industrial management united by the tie rods of a high sense of human values and relations are essential for t h e productivity of such a business. Products are created b y the research chemist, studied and developed by highly trained physicists, biologists, engineers, and technologists, and then fashioned t o meet the needs of society b y a host of workers in varied fields of application. M o s t of the synthetic dyes and allied products have no counterparts in Nature. The natural coloring agents have been replaced for the most part by products which are built up from colorless substances or materials incapable of imparting color of lasting value and beauty. These dyes and related substances owe their chemical allegiance t o lowly ancestors. From the common things about us —coal, sulfur, salt, minerals, air, and water—the chemist constructs the building stones of t h e complex molecular structures of the modern dyes, pigments, drugs, vitamins, perfumes, resins, fibers, cleansing agents, antioxidants, accelerators, and m a n y other products of value in providing the things that are necessary for t h e fullness of modern life. All the colors of the rainbow, t h e delicate perfume of the array of flowers in a beautiful garden, the tonic needed by rubber to stand the bruising punishment of t h e road, and the molecular bullets t h a t stop the invasion of microbes into t h e human system, thus minimizing the hazards of disease and staying the sickle of Death, are often close chemical relatives, having been derived from the same essential raw materials and intermediates. The same molecular building stones m a y serve for the construction of widely different chemical structures of varied properties which make t h e m useful in industry. These chemical building stones are comparatively simple organic substances. T h e y do n o t exist ready formed i n coal and other natural materials so t h a t they m a y b e sifted o u t b y mechanical means. T h e y m u s t be envisaged b y t h e chemist and then cleaved out of the raw materials or built u p from t h e fragments chipped off the molecular structures present i n these materials. The research chemist must 1 Presented before the Northern N e w England Section of the A. A. T. C. C , January 17, 1941
fashion in his mind the picture of what he wishes t o create and then plan t h e means by which it m a y be made a reality. Of course not all of the pictures t h a t the mind sees are realizable. There are so m a n y gaps in the fundamental knowledge essential t o an understanding of these mental pictures and t h e means of making t h e m real that only a small percentage ever become actualities. Also t h e best planned investigations often fail because of inability to comprehend the full significance of the evidence based o n the experimental facts. Often t h e results achieved are quite different from those predicted. This is due in large measure to the limited knowledge on which t o base a prediction. The important thing for the scientific investigator is that he should be able to recognize what is significant in the results of an investigation and formulate the knowledge into a workable useful tool capable of being operated by nontechnical m e n a t maximum efficiency and product i v e capacity. T h e growth of the d y e and related products industry has been greatly stimulated by the hormone of research. This research has assured the growth process and at the same time protected the developing structure against the depletive influence of unrestricted economic forces. Fundamental research is essential t o find the combinations that will unlock t h e treasure vaults of science and technology and make available the knowledge needed t o create n e w products, improve old ones for greater usefulness, and make cheaper the products of proved value. Unlike most industries, t h e dye and allied products industry has no normalcy. N o products t h a t it makes are ever good enough and staple enough t o hold constantly a place in the ever-changing picture of this industrial age. B y research the industry m u s t be in a position t o offer products which do a better job of service tomorrow than the products available do today. There is nothing fixed in this industry. T h e constant demand for change to meet competition is costly, b u t this is the price that must be paid for progress. T h e cost is more t h a n offset b y gains in social and economic developments, with resulting benefits t o mankind. T h e results of such research benefit t h e consumer of m a n y and widely different products. They m a k e it possible for the manufacturer to render better and better service. This is true independent of the nature of the research problem. If it is worth solving the result must be of benefit t o someone, somehow. I t m a y be the burning of ammonia t o make nitric acid, making of a rubber accelerator, synthesis of silk or rubber, creation of a new dye or 629
drug, or study of the chemistry of infectious diseases; ultimately it will benefit society, whether it be in getting more for the dollar or in greater safeguards against the hazards of life. Research is the whippletree which serves t o harness the team of science and technology t o the plough of industry. I t must be competent and effective. I t is not magic. It is creative work and requires a select, highly trained personnel capable of visualizing the specifications for the things that will serve t o enrich life and having the capacity for great achievements. I t must be properly directed by men of vision, wide proficiency of knowledge, expertness, a tolerant understanding of human weaknesses, sound judgment, and great inspirational leadership. Research chemists, as other creative types, should possess three mental attributes—an insatiable desire t o know, vivid imagination which is capable of being disciplined, and originality or that capacity to find new frames of references into which new observations will best fit to give t h e most satisfying and useful pictures for the interpretations of Life's truest values. N o t every man who studies chemistry is capable of doing research. Of course this term is badly misused. Much t h a t is mere "pot boiling" in chemistry often passes for research and creative and noncreative types of chemists are t o be found marching forward under t h e banner of research in the best of laboratories. This is because there is important, useful work t o be done b y both types, and i t is not always easy t o draw a sharp line of distinction between the contributions made. So m a n y factors go to make up success, in research as well as in other types of human service, that it is often difficult t o pick out the one of greatest value. Industry, stability, initiative, and pleasing personality frequently combine t o win a place on a research team for a chemist who does not possess the essential attributes for creative work. This is as it should be. T h e strong balance the weak and the united effort of the team is what counts in its effectiveness in an organization. T h e problems involved in the manufacture of dyes and allied products are numerous and varied in kind and complexity. T o synthesize a dye capable of producing a definite color is in itself a difficult task but to succeed in giving it the working properties and color of the degree of fastness and purity of tone desired is e v e n more difficult. M a n y products m u s t be made in our present state of knowledge before t h e desired properties are obtained. Although there are certain principles which are helpful in planning dye.
NEWS
630 molecules, it is not y e t possible to design and build them to specifications. Trial and error still play an important role in chemical research. The desired effect may not be attainable with one dye and when two or more must be mixed to pro duce the color new problems arise. To solve these often it is necessary to under take research in certain phases of physical chemistry which, at first glance, would seem far afield. The hue obtained will depend upon the proper ratio of the blend of colors on the fiber and of course the rate of absorption and distribution of the colors in t h e fiber may be different under the conditions of the practical usage of the mixture. T o select the components of the mixture to work properly data must be available of the exact behavior and the effect of each component on the other. This frequently involves several different investigations in organic, physical, and textile chemistry. Definite color changes are associated w i t h structural changes in the dye mole cules, but this means of obtaining the variations in colors will not give the many h u e s and tones of color required for the variegated patterns in use today. T o pro d u c e an individual dye for every tone of color needed would greatly complicate the business and increase the cost of both dyes and t h e goods colored with them. How ever, a great variety of hues can be pro duced with dyes of discrete structure and research constantly adds t o the number. Starting with benzene, toluene, and naphthalene many intermediates are made a n d from these are derived most of the d y e s and organic pigments in use today.
EDITION
Vol. 19, No. 11 ing, whereas color harmony is dependent upon the proper molecular selection of the components of light required to give the desired effect. Dyes and pigments do this by having in their structure atomic groxips which pick out certain light waves from the jumble of light waves that make up -white light and allow only definite char acteristic colored light to pass. The mo lecular structure of the coloring agent is therefore highly important and a knowl edge of the relation between color and molecular architecture is an essential part of the fundamental research underlying the synthesis and development of dyes and pigments. T h e manufacture of dyes and pigments is closely interwoven with the production of many other organic products. Often t h e same intermediates that are needed for valuable coloring agents will serve as the paxent compounds for drugs, perfumes, explosives, and many other products hav i n g widely different uses. Aniline is an important intermediate for certain dyes b u t it i s also the parent compound of m a n y useful therapeutic agents, including t h e sulfanilamides. The wheels of re search turn in one direction and the results a r e products that are capable of producing a l l the colors of the rainbow; they turn in another and t h e automobile owner is as sured better and cheaper tires; and still another and there is obtained the means of safeguarding health and reducing the haz ards of life. The ever-occurring question is to what new use can the allied products o f dye manufacture be put to increase the frailness of life and t o help secure the fruits of prosperity for all mankind.
B y one series of reactions benzene is the parent of a family of azo dyes capable of giving a wide variety of colors of different degrees of brightness and permanence. T h e essential intermediate in this series is aniline. It and its derivatives hold a promi nent place in the aristocracy of color. One branch of the family owes its impor tance t o its union with the naphthols or derivatives of naphthalene. T h e colored descendants include yellows, reds, oranges, violets, and blues and among them are well-known dyes like orange II and direct black. Other important families of dyes in which aniline is a chemical partner in clues such important members as methyl violet, methylene blue, indigo, induline, and fuchsine. The dye molecules may vary widely in complexity with correspond ing differences in the difficulties in manu facture. Some require but a few chemical steps and others involve many. Some are extremely complicated and costly. Benzene and its close relative toluene give derivatives which enter into t h e manufacture of many valuable dyes and pigments. B y the combination of these parent compounds with other structures important products such as the alizarines, indanthrenes, thioindigoes, and sulfur dyes are obtained. The entire pageantry of color in the industrial and domestic arts depends upon the availability of synthetic dyes. The harmony of suitable colors in producing a pleasing effect is as essential t o an artistic design as the proper selection and arrangement of musical tones to a great symphony. Good music is the re sult of the art of blending many sounds which individually may not be fully pleas
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Commercial Solvents Comes of A g e T h e 21 s i birthday of Commercial Solvents was celebrated M a y 8 with a dinner-dance at Terre Haute, Ind., where the parent plant is located. More than 600 persons were present including executives from the N e w York office and other plants of the corporation. Henry
E . Perry, vice presidecnt, w a s toast-master, and T. P . Walker, president, delivered an address. Featured event was formation of tr*e Twenty Year Club. Maynard C. .Wheeler, production manager, presented the 35 candidates, and Major Wal&er gave a gold watch to each.
NEWS
June 10, 1941
EDITION
A . C. S. Student Membership Awards for 1 9 4 0 DONOR
RECIPIENT
Alpha Chi Sigma Fraternity Alpha Kappa Chapter. This award, consisting of member- Harry F. Kauffman, Jr. ship and a subscription to one journal, is given to the senior in chemistry or chemical engineering at the Uni versity of Virginia having the highest scholastic average. Rho Chapter. Annual award, consisting of membership Arthur Thomas Sweet, Jr. and a subscription to one journal, is given to the out standing senior receiving a B.S. degree in chemistry at the University of North Carolina. Gamma Sigma Epsilon Chemical Fraternity. Memberships are awarded annually by the fraternity to the most out standing student in each chapter. Alpha Beta Chapter, North Carolina State College. Edwir. R. Todd Delta Beta Chapter, University of Alabama. John Key McKinley Phi Lambda Upsilon Fraternity Upsilon Chapter. This award, consisting of membership Walter C. Brandsma and a subscription to one journal, is given t o the senior student in cnemistry and chemical engineering at the University of Iowa with the highest grade record for his four years of study. Xi Chapter. Annual award, consisting of membership and Ernest S. Elyash a subscription to one journal, is presented annually to the highest ranking sophomore pursuing the bachelor of science course in chemistry at the University of Pitts burgh. Edward Bartow. Annual membership award to the out Eldon E. Bauer standing graduate student in chemistry at The State University of Iowa. Northeast T e n n e s s e e Section, AMERICAN CHEMICAL SOCIETY. Charles C. Neas The recipient of this award, a student a t the Tennessee State Teachers College, was chosen as the winner for having presented the best paper among those written by chemistry students from the colleges within the Northeast Tennessee Section. His paper was entitled "The Chemotherapy of Sulfanilamide". Alexander Silverman. Annual award to t h e student at the Ernest L. Wimmer University of Pittsburgh who is a candidate for the B.S. degree in chemistry, having the highest average rating for his first three years.
ton, Ala., but the division also has plants in Monsanto, Tenn., and Carondelet, Mo., and a fourth under construction at Trenton, Mich.
631 Department of the Koppers Co., F. W . Jung has been transferred t o the com pany's Seaboard Laboratories at Kearny, N. J. Joseph B . Kushner, metal finishing con sultant and engineer, has moved his offices and laboratories t o larger quarters at 114 East 32nd St., N e w York, Ν. Υ. He was formerly at 126 West 32nd St. R. W . Leslie has resigned his position as director of Research and Process De velopment with the Skelly Oil Co., El Dorado, Kans., which he has held for the past 11 years, to become manager of Refinery Operations for t h e Wasatch Oil Refining Co., Salt Lake City, Utah, and t h e Idaho Refining Co., Pocatello, Idaho. H. J. Lynch has been appointed the new representative of Morris Machine Works, Baldwinsville, Ν. Υ., in the Detroit district. He is located at 403 Kales Bldg., Detroit. W. C. Pinkerton, for the past six years an assistant technical editor of Chemical Engineering Catalog, has joined t h e Monel and Rolled Nickel Advertising Department of The International Nickel Co. H e will edit house publications de voted t o the process industries. Newly elected officers of the New York Section of the American Institute of Chemists are Donald Price, chairman, Elmore Northey, vice chairman, and Milton Burton, secretary-treasurer.
The Geological Society, England, has awarded its highest honor, The Wollaston Medal to Arthur L. Day, director of the Geophysical Laboratory of Wash ington from 1907 to 1937, for his re searches in vulcanology and in the field of experimental petrology. Robert Rast Cole, general manager of Monsanto's Phosphate Division, has been elected t o a vice presidency of the company. Mr. Cole is located in Annis-
Jerome F. Grattan, formerly research chemist a t the Squibb Institute, has joined the recently organized research staff of the International Vitamin Corp., N e w York, Ν . Υ . Leland H . Greneli, for the past five years with the Frigidaire Division of General Motors, has been engaged b y Battelle Memorial Institute for research and development work in t h e rapidly grow ing new products research of the insti tute. J. L. Heid, formerly in charge of the U. S. Fruit and Vegetable Products Labora tory, has resigned to accept a position as chemist and production manager with the California Citrus Juice Exchange, Inc., Santa Ana, Calif.
Robert R. Cole
Previously a research consultant in Pitts burgh and more recently of the Research
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C. F. Rassweiler, director of the Phila delphia laboratory of E . L du Pont de Nemours & Co., Inc., has been ap pointed director of research of JohnsManville Corp., Manville, N . J. I n his new position Dr. Rassweiler will be a member of the Officers Board in charge of Johns-Manville's research activities on which the company is spending close to $1,000,000 a year. John D . Sullivan, chief chemist, Battelle Memorial Institute, Columbus, Ohio,
