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ylide pigment - Wikipedia, the free encyclopedia

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Diarylide pigmentom Wikipedia, the free encyclopedia

arylide pigment s are organic compounds that are used as pigments in inks and related materials. Theyen are yellow or yellow-green. To some extent, these organic compounds have displaced cadmium sulfim the market. They exist as yellow powders of low solubility in water. [1]

Contents

1 Production2 Uses

3 Toxicity and hazards4 See also5 References

roduction

e formation of these pigments involves the reaction of diazotized aromatic diamines (derivatives of nzidine ) with coupling components, typically derivatives of acetoacetanilide . By varying both of thesemponents, a wide variety of pigments have been produced. [2] A related family of organic pigments are the

mpler arylides , which arise from the coupling of monodiazonium salts with the same coupling partners.

e molecular structures of these molecules is more conjugated than represented in the images shownlow. [3] The pigments' colors can range from yellow to green. One of the most common diarlyide yellowgments is Pigment Yellow 12 . Its CAS number is 6358-85-6 (http://www.emolecules.com/cgi-bin/search?ss&q=6358-85-6&c=1&v=) . Other diarylide yellow pigments include yellow 13 5102-83-0tp://www.emolecules.com/cgi-bin/search?t=ss&q=5102-83-0&c=1&v=) , yellow 17 4531-49-1tp://www.emolecules.com/cgi-bin/search?t=ss&q=4531-49-1&c=1&v=) and yellow 83 5567-15-7tp://www.emolecules.com/cgi-bin/search?t=ss&q=5567-15-7&c=1&v=) . These pigments share the sameckbone and vary in color depending on substitution of the benzene rings. Worldwide production of colorganic pigments was estimated to be about 250,000 metric tons (t) in 2006, with about 25%, or 62,500 t,ing diarylide yellows. [4]

ynthesis of C.I. Pigment Yellow 12, a diarylide pigment.

http://en.wikipedia.org/wiki/Organic_compoundhttp://en.wikipedia.org/wiki/Cadmium_sulfidehttp://en.wikipedia.org/wiki/Diazonium_salthttp://en.wikipedia.org/wiki/Benzidinehttp://en.wikipedia.org/wiki/Acetoacetanilidehttp://en.wikipedia.org/wiki/Arylide_yellowhttp://en.wikipedia.org/wiki/CAS_numberhttp://www.emolecules.com/cgi-bin/search?t=ss&q=6358-85-6&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=5102-83-0&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=4531-49-1&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=5567-15-7&c=1&v=http://en.wikipedia.org/wiki/File:PigmentYellow12corrected.pnghttp://www.emolecules.com/cgi-bin/search?t=ss&q=5567-15-7&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=4531-49-1&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=5102-83-0&c=1&v=http://www.emolecules.com/cgi-bin/search?t=ss&q=6358-85-6&c=1&v=http://en.wikipedia.org/wiki/CAS_numberhttp://en.wikipedia.org/wiki/Arylide_yellowhttp://en.wikipedia.org/wiki/Acetoacetanilidehttp://en.wikipedia.org/wiki/Benzidinehttp://en.wikipedia.org/wiki/Diazonium_salthttp://en.wikipedia.org/wiki/Cadmium_sulfidehttp://en.wikipedia.org/wiki/Organic_compound

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Diarylide pigments

ses

e diarylide yellows are the most common yellow pigments used in printing as well as a wide variety of otherplications. Due to their stability, diarylide yellows are used in inks , coatings, and many plastics . The

gment is insoluble. It is a standard pigment used in printing ink and packaging industry. The diarylide yellowgment Yellow 12 is one of the three main colored pigments used in the four color process of color printinsuch, its use is ubiquitous in printing both in commercial applications and in home color printers, as well astextile printing.

oxicity and hazards

arylide yellow pigments are considered to be non-toxic. However, there is some evidence that thesegments can break down when exposed to temperatures above 200 degrees C to release3'- Dichlorobenzidine , which is a carcinogen and is listed in the U.S. EPAs Toxics Release Inventory .

igment Yellow 13 & 34 (R = H or Me) Pigment Yellow 83

igment Yellow 81 Pigment Yellow 17

igment Yellow 14 Pigment Yellow 16

http://en.wikipedia.org/wiki/Inkhttp://en.wikipedia.org/wiki/Plastichttp://en.wikipedia.org/wiki/Color_printinghttp://en.wikipedia.org/wiki/Textile_printinghttp://en.wikipedia.org/wiki/Dichlorobenzidinehttp://en.wikipedia.org/wiki/Toxics_Release_Inventoryhttp://en.wikipedia.org/wiki/Pigment_Yellow_16http://en.wikipedia.org/wiki/Pigment_Yellow_16http://en.wikipedia.org/wiki/Toxics_Release_Inventoryhttp://en.wikipedia.org/wiki/Dichlorobenzidinehttp://en.wikipedia.org/wiki/Textile_printinghttp://en.wikipedia.org/wiki/Color_printinghttp://en.wikipedia.org/wiki/Plastichttp://en.wikipedia.org/wiki/Inkhttp://en.wikipedia.org/wiki/File:YellowPig5thTry.pnghttp://en.wikipedia.org/wiki/File:PigmentYellow14.pnghttp://en.wikipedia.org/wiki/File:PigmentYellow17.pnghttp://en.wikipedia.org/wiki/File:PigmentYellow81.pnghttp://en.wikipedia.org/wiki/File:PigmentYellow83.pnghttp://en.wikipedia.org/wiki/File:PigmentYellow13%2634.png

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ylide pigment - Wikipedia, the free encyclopedia

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arylide yellow pigments using 3,3-dichlorobenzidine were developed to avoid the toxicity issues of nzidine-based pigments. 3,3-dichlorobenzidine is structurally similar to one of the polychlorinated biphenyngeners, PCB 11 (3,3-dichlorobiphenyl), and there is some evidence that the use of diarylide yellowgments introduces PCB 11 to the environment. [5][6]

ee also

List of colours

eferences

1. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, Weinhei2012. doi :10.1002/14356007.a20_371 (http://dx.doi.org/10.1002%2F14356007.a20_371)

2. ^ Lewis, D. M., Modern colorants synthesis and structure. Advances in color chemistry series, Vol. 3. Edited by A. T.Peters & H. S. Freeman, Blackie Academic & Professional, Glasgow, 1995, xii + 245 pp. ISBN 0 7514 0209 5. JournaChemical Technology & Biotechnology 1996, 65, (2), 207-208.

3. ^ Barrow, M. J.; Christie, R. M.; Monteith, J. E., The crystal and molecular structures of three diarylide yellow pigments,C. I. Pigments Yellow 13, 14 and 63. Dyes and Pigments 2002, 55, (2-3), 79-89.

4. ^ Savastano, D., The pigment report: although 2006 was a year of improvement, pigment manufacturers are copingwith a wide variety of challenges, including raw material pricing and supply issues and overcapacity. Ink world 2007,March.

5. ^ Rodenburg, L. A.; Guo, J.; Du, S.; Cavallo, G. J., Evidence for Unique and Ubiquitous Environmental Sources of 3,3'-Dichlorobiphenyl (PCB 11). Environmental Science & Technology 2009, 44, (8), 2816-2821.

6. ^ http://ehp.niehs.nih.gov/121-a86/ (http://ehp.niehs.nih.gov/121-a86/})

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tegories : Pigments Organic pigments Shades of yellow Azo compounds Azo dyes

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