Diarylide pigment - Wikipedia, the free encyclopedia

Diarylide pigment
From Wikipedia, the free encyclopedia

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

Contents
1 Production
2 Uses
3 Toxicity and hazards
4 See also
5 References

Production

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

The formation of these pigments involves the reaction of diazotized aromatic diamines (derivatives of
benzidine) with coupling components, typically derivatives of acetoacetanilide. By varying both of these
components, a wide variety of pigments have been produced. [2] A related family of organic pigments are the
simpler arylides, which arise from the coupling of monodiazonium salts with the same coupling partners.
The molecular structures of these molecules is more conjugated than represented in the images shown
below. [3] The pigments' colors can range from yellow to green. One of the most common diarlyide yellow
pigments is Pigment Yellow 12. Its CAS number is 6358-85-6 (http://www.emolecules.com/cgi-bin/search?
t=ss&q=6358-85-6&c=1&v=) . Other diarylide yellow pigments include yellow 13 5102-83-0
(http://www.emolecules.com/cgi-bin/search?t=ss&q=5102-83-0&c=1&v=) , yellow 17 4531-49-1
(http://www.emolecules.com/cgi-bin/search?t=ss&q=4531-49-1&c=1&v=) and yellow 83 5567-15-7
(http://www.emolecules.com/cgi-bin/search?t=ss&q=5567-15-7&c=1&v=) . These pigments share the same
backbone and vary in color depending on substitution of the benzene rings. Worldwide production of color
organic pigments was estimated to be about 250,000 metric tons (t) in 2006, with about 25%, or 62,500 t,
being diarylide yellows. [4]
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Diarylide pigment - Wikipedia, the free encyclopedia

Diarylide pigments

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

Pigment Yellow 83

Pigment Yellow 81

Pigment Yellow 17

Pigment Yellow 14

Pigment Yellow 16

Uses
The diarylide yellows are the most common yellow pigments used in printing as well as a wide variety of other
applications. Due to their stability, diarylide yellows are used in inks, coatings, and many plastics. The
pigment is insoluble. It is a standard pigment used in printing ink and packaging industry. The diarylide yellow
pigment Yellow 12 is one of the three main colored pigments used in the four color process of color printing.
As such, its use is ubiquitous in printing both in commercial applications and in home color printers, as well as
in textile printing.

Toxicity and hazards

Diarylide yellow pigments are considered to be non-toxic. However, there is some evidence that these
pigments can break down when exposed to temperatures above 200 degrees C to release
3,3'-Dichlorobenzidine, which is a carcinogen and is listed in the U.S. EPAs Toxics Release Inventory.
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Diarylide pigment - Wikipedia, the free encyclopedia

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

See also
List of colours

References
1. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, Weinheim,
2012. 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. Journal of
Chemical 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 coping
with 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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Categories: Pigments Organic pigments Shades of yellow Azo compounds Azo dyes
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