Arylide yellow

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Arylide yellowHow to read this color infobox
About these coordinates     Color coordinates
Hex triplet #E9D66B
sRGBB  (rgb) (233, 214, 107)
CMYKH   (c, m, y, k) (0, 8, 54, 9)
HSV       (h, s, v) (51°, 54%, 91%)
Source [1] [2]
B: Normalized to [0–255] (byte)
H: Normalized to [0–100] (hundred)

Arylide yellow, also known as Hansa Yellow and Monoazo yellow, are a family of organic compounds used as pigments. They are primarily used as industrial colorants including plastics, building paints and inks. They are also used in artistic oil paints and watercolors. These pigments are usually semi-transparent yellows and yellow-greens. Related organic pigments are the diarylide pigments. Overall, these pigments have partially displaced cadmium yellow in the marketplace.

Production[edit]

The compound is obtained by azo coupling of aniline and acetoacetanilide or their derivatives. The class of compounds was discovered in Germany in 1909.[1]

Synthesis of Hansa Yellow Pigments, R and R' represent a variety of substituents.

Examples[edit]

Members of this class include:

  • Pigment Yellow 6 (CAS # 2512-29-0), derived from 4-chloro-2-nitroaniline (diazonium precursor) and aniline (acetoacetanilide precursor) to produce medium yellows.
  • Pigment Yellow 3 (CAS # 6486-23-3), derived from 4-chloro-2-nitroaniline (diazonium precursor) and 2-chloroaniline (acetoacetanilide precursor) to produce greenish-yellows.
  • Pigment Yellow 16 derived from 2,4-dichloroaniline (diazonium precursor) and o-tolidine (acetoacetanilide precursor) to produce medium-yellows.
  • Pigment Yellow 74 (CAS # 6358-31-2), derived from 2-methoxy-4-nitroaniline (diazonium precursor) and 2-methoxyaniline (acetoacetanilide precursor) to produce greenish-yellows.

Pigment Yellow 16

Maimeri, an Italian paint manufacturer, combines arylide yellow with yellow iron oxide and zinc oxide to create their version of Naples yellow light.

See also[edit]

References[edit]

  1. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371