Aldolf von Baeyer, at the age of 13, embarked on the study of indigo. In his work withindigo, von Baeyer had developed the technique of removing oxygen to producesimpler compounds. Two students, Carl Graebe and Carl Liebermann applied thistechnique of heating compounds in zinc to alizarin resulting in anthracene. Theythen decide to reverse the process and add oxygen to anthracene. Although theirprocedure was illogical, they were the first to synthesize a natural dye, alizarin,previously obtained from natural sources like the madder plant.

Aldolf von Baeyer deduced the structure of indigo and carried out several syntheses.None were economically profitable. in 1883, Karl Heumann at Badische Anilin-undSoda-Frabrik Company (BASF) developed the first successful commercialsynthesis of indigo. A chemist, by the name of Sapper, heating naphthalene withfuming sulfuric acid broke a mercury thermometer in the mixture. The resultingmercury sulfate was the catalyst need to oxidize the naphthalene into phthalicanhydride which can be converted into dyes.

A. G. Dandridge produced phthaloctanine when ammonia was passed throughmolten phthalic anhydride in 1928. The mixture reacted with the iron vesselproducing a blue crystal. With the use of x-ray diffraction techniques, R. P. Linsteadanalyzed the blue crystals discovered by Dandridge. Linstead noted that theformulas were similar to the pigmenting units of blood in which the central metalatom was iron. He substituted copper for the iron producing "monastral blue" nowused in color printing. By substituting several hydrogens with chlorines, copperphthalocyanine yields an excellent green pigment.

Today, the manufacturing of cosmetics and synthetic dyes are among the greatestmoney producers. The chemical industry of Europe grew out of the dye industry.Today, new dyes are being produce to adhere to modern synthetic fabrics. M&MTMand CrayolaTM have looked for new colors to market their products. Therefore, theimportance to the profession is as changing as the colors.

HUMOR: ON 1. In 1800, Benjamin Franklin said " about light, I am in the dark."

THE HUMAN 2. Beer's Law states: the taller the glass, the darker the brew, less light passes through

3.The dye makers' convention was held in a tint; 4. Litmus is a lye detector.

I

INSTRUMEN- TATION

MEDIA

SIDE

http://www.jce.divched.org/JCEDLib/WebWare/index.html SpecScan: A Utility Program for Generating Numerical Data from Printed Forms of Spectra or Other Signals Constantinos E. Efstathiou Obtaining digital data from analog figures is made much easier using this Windows utility. After scanning and touching-up a figure, you can import it into SpecScan to obtain X–Y data, which can then be exported to Excel or other program for additional processing. “The World of Chemistry” Video 2 “Color” Annenberg CPB (www.learner.org) Spectrophotometer, Instrumentation Module (INST, p. 4) X-Ray Diffraction Techniques

44 The Chemistry of Color (COLR)

References

The Chemistry of Color (COLR) 49a

Orna, M. V. ((1978 Winter) The Chemistry behind the Artist's Palette. COLOR Research & Application. John Wiley & Sons, Inc. 3 (4). Mary Virginia Orna, 0 S U links together the physics of the light source, the chemistry of the light modification, and the psychophysical response. The article gives background on a variety of pigments including history, chemical composition, and color properties.

(1980 April) Chemistry and Artists' Colors. Three parts. Journal of Chemical Education. 57 (4), 256-258, 264-267, 267-269.

This three part series is a condensed version of the textbook of the same title. These articles are not only recommended reading but a must reading for depth of understanding. This module is based upon the information contained in the article.

Orna, M.V. and Goodstein, M.P. (1993) Chemistry and Artists' Colors. 2nd Edition. College of New Rochelle, NY. This textbook contains detailed information on the subject. The text is also very well written at a level of understanding for the elementary and secondary teacher. This text is a good source for overheads. Unfortunately, you have to stand on your head to read the diagram on p. 248!

Reynolds, R. C. and Comber, R. N. (1994 December) The ABC's of Chromatograghy. Journal of Chemical Education. 71 (12), 1075-1077.

This article explains how the separation of dye with a TLC column of seven dyes can produce not only the alphabet but a colorful demonstration.

Rossotti, H. (1983) Colour, Why the World Isn't Grey. Princeton Science LIBRARY. Princeton: Princeton University Press. Hazel Rossotti uses matter, energy, and the eye to discuss the colours of the natural world, the mechanism of color vision, and a range of color technologies. The book deals with the relationship of physics and chemistry of light to dyes, animal and vegetable colors, and color perception. The latter chapters describe the relationship of color to human sensations.

Simon, M. S. (1994 February) New Developments in Instant Photography. Journal of Chemical Education. 71(2), 132-140. A detailed explanation of the theory of instant color photography is described. Various dyes used to produce colors are of interest.

Smith, P. E. and others. (1992 October) A Multicolored Luminescence Demonstration. Journal of Chemical Education. 69 (10) 827-828. The article explains how to use different dyes or sensitizers to change the color of luminol oxidation.

Thomas, N. C. (1990 April) A Chemiluminescent Ammonia Fountain. Journal of Chemical Education. 67(4), p.339. This demonstration combines an ammonia fountain with chemiluminescence.

Wilcox, M. (1994) Blue and Yellow Don't Make Green or How to Mix the Color You Want. Cincinnati: Every Time North Light. This paperback contains information on the theory and practice of mixing pigments or paints for the desired color. The most interesting theory section, Color Wheel Bias, contains information as to why the color wheel should be eliminated.

References

Updates by James O. Schreck and Mary Virginia Orna Activities JCE Classroom Activity (1997). “Anthocyanins: A Colorful Class of Compounds.” Journal of Chemical Education 74, 1176A-B. (Has Classroom Connections.) JCE Classroom Activity (1998). “How Many Colors in Your Computer? Discovering the Rules for Making Colors.” Journal of Chemical Education 75, 312A-B. JCE Classroom Activity (1999). “The Effects of Temperature on Lightsticks.” Journal of Chemical Education 76, 40A-B. JCE Classroom Activity (1999). “Colors to Dye For: Preparation of Natural Dyes.” Journal of Chemical Education 76, 1688A-B. JCE Classroom Activity (2000). “The Write Stuff: Using Paper Chromatography to Separate an Ink Mixture.” Journal of Chemical Education 77, 176A-B. JCE Classroom Activity (2001). “LEDs Are Diodes.” Journal of Chemical Education 78, 1664A-B. JCE Classroom Activity. (2003). “Out of the Blue..” Journal of Chemical Education, 80, 536A- B. JCE Classroom Activity. (2004). “Flame Tests: Which Ion Causes the Color?” Journal of Chemical Education, 81, 1776A- B. JCE Classroom Activity. (2005). “Colors in Liquid Crystals.” Journal of Chemical Education, 82, 1360B. JCE Classroom Activity. (2007). “Cooking Up Colors from Plants, Fabric and Metal.” Journal of Chemical Education, 84, 96A- B. JCE Classroom Activity. (2007). “How Does Your Laundry Glow?.” Journal of Chemical Education, 84, 800A- B. JCE Classroom Activity. (2007). “Fluorescent Fun: Using a Homemade Fluorometer.” Journal of Chemical Education, 84, 1312A- B. JCE Classroom Activity. (2007). “How Does Your Laundry Glow?.” Journal of Chemical Education, 84, 800A- B. JCE Classroom Activity. (2007). “Colorful Lather Printing.” Journal of Chemical Education, 84, 608A- B. References (1999) “Colors to Dye for: Preparation of Natural Dyes,” Journal of Chemical Education, 76, 1688A. Describes how to make dies from natural sources, a mordant is used, and then fibers are dyed.

The Chemistry of Color (COLR) 49b

Aurian-Blajeni, B., Sam, J., & Sisak, M. (1999) “Sweet Chemistry,” Journal of Chemical Education, 76, 91. An experiment performing spectrophotometry on food dies and brown M&M candy, corresponding colors with spectral features. Bosma, W. (1998) “Using Chemistry and Color To Analyze Household products: A 10-12 Hour Laboratory Project at the General Chemistry Level,” Journal of Chemical Education, 75, 214. An analysis of different household products using a spectrometer, indicators, and chromatography. Denio, A. (2001) “The Joy of Color in Ceramic Glazes with the Help of Redox Chemistry,” Journal of Chemical Education, 78, 1298. Discuses how oxidative and reductive processes influence the color formed in glazes used on clay. Elsworth, J. (2000) “Entertaining Chemistry—Two Chemical Reactions,” Journal of Chemical Education, 77, 484. Solutions of acid and iodine, with and without starch, are mixed with alkaline solutions containing thiosulfate and appropriate salts to produce desirable color effects. Epp, D., Sarquis, M. (1995) The Chemistry Vat Dyes, Palette of Color Series. Terrific Science Press, Miami University: Middletown, OH. Flinn Scientific Catalog Number AP9125. Epp, D., Sarquis, M. (2000) The Chemistry Food Dyes, Palette of Color Series. Terrific Science Press, Miami University: Middletown, OH. Flinn Scientific Catalog Number AP9125. Epp, D., Sarquis, M. (1995) The Chemistry Natural Dyes, Palette of Color Series. Terrific Science Press, Miami University: Middletown, OH. Flinn Scientific Catalog Number AP9125. Flinn Chemistry Activity Book. Chemistry of Color. Flinn Scientific Catalog Number AP4281. Gettys, N. (1999) “Pushing the Rainbow: Frontiers in Color Chemistry; Light and Color in Chemistry-Report on Two American Chemical Society Presidential Events,” Journal of Chemical Education, 76, 737. An exploration of various aspects of the importance of light and color in chemistry. Gettys, N. (2001) “Pigments of Your Imagination: Making Artist’s Paints,” Journal of Chemical Education, 78, 1320A. Discusses how to make paint, and the chemistry behind the paint. Greenberg, B.R., Patterson, D. (2008) Art in Chemistry; Chemistry in Art. Greenwood Press: Westport, CT. Hughes, J. (1998) “Thermochromic Solids,” Journal of Chemical Education, 75, 57. A look at why certain chemicals chance colors as they are heated and cooled. Jacobs, S. (1997) “Challenges of Everyday Spectra,” Journal of Chemical Education, 74, 1070. Suggestions on how to help students understand the spectra of different elements, and suggests teachers to encourage their students to go out and look at the spectra of neon lights around town. The Chemistry of Color (COLR) 49c

JCE Editorial Staff. (1998) “How Many Colors in Your Computer? Discovering the Rules for Making Colors,” Journal of Chemical Education, 75, 312A. A look at how just using red, blue and green pixels, we see colors through our computer screen, and how computer screens work.

JCE Editorial Staff (2008) “Using ‘Blueprint Photography by the Cyanotype Process,’” Journal of Chemical Education 85, 620-621.

Orna, M. (2001) “Chemistry, Color, and Art,” Journal of Chemical Education, 78, 1305. Discusses how chemistry and art converge when it comes to color.

Rigos, A. & Salemme, K. (1999) “Photochemistry and Pinhole Photography: An Interdisciplinary Experiment,” Journal of Chemical Education, 76, 736A. Discusses a method for making a pinhole camera, and explains the chemistry involved in black and white photographs.

Schatz, P. (2001) “Indigo and Tyrian Purple—In Nature and in the Lab,” Journal of Chemical Education, 78, 1442. The use and synthesis of the dyes indigo and Tyrian purple are discussed. Smith, A.E., Hiroshi Mizoguchi, H., Delaney, K., Spaldin, N.A., Sleight, A.W., Subramanian, M.A. (2009) “Mn3+ in Trigonal Bipyramidal Coordination: A New Blue Chromophore,” J. Am. Chem. Soc., 131 (47), pp 17084–17086 This paper describes the accidental discovery of a new blue pigment that may be the route to a family of environmentally benign, chemically and thermally stable, bright blue inorganic pigments.

Soldat, D.J., Barak, P., Lepore, B.J. (2009) “Microscale Colorimetric Analysis Using a Desktop Scanner and Automated Digital Image Analysis,” Journal of Chemical Education, 86, 617-620.

Steinhart, C. (2001) “Biology of the Blues: The Snails behind the Ancient Dyes,” Journal of Chemical Education, 78, 1444. A look at the three species of snails that were used in the ancient Mediterranean industry, and the colorless dye precursors that are secreted from these animals.

Ware, M. (2008) “Prussian Blue: Artists’ Pigment and Chemists’ Sponge,” Journal of Chemical Education 85, 612-619.

White, M. (1998) “The Chemistry behind Carbonless Copy Paper,” Journal of Chemical Education, 75, 1119. A description of how carbonless carbon paper works.

The Chemistry of Color (COLR) 49d