Arylide yellow, also known as Hansa yellow and monoazo yellow, is a family of

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

s used as

pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic comp ...

s. They are primarily used as industrial colorants including

plastics Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...

, building paints and inks. They are also used in artistic

oil paint Oil paint is a type of slow-drying paint that consists of particles of pigment suspended in a drying oil, commonly linseed oil. The viscosity of the paint may be modified by the addition of a solvent such as turpentine or white spirit, and varn ...

s, acrylics and

watercolors Watercolor (American English) or watercolour (British English; see spelling differences), also ''aquarelle'' (; from Italian diminutive of Latin ''aqua'' "water"), is a painting method”Watercolor may be as old as art itself, going back to ...

. These pigments are usually semi-transparent and range from orange-yellow to yellow-greens. Related organic pigments are the diarylide pigments. Overall, these pigments have partially displaced the toxic

cadmium yellow Cadmium pigments are a class of pigments that contain cadmium. Most of the cadmium produced worldwide has been for use in rechargeable nickel–cadmium batteries, which have been replaced by other rechargeable nickel-chemistry cell varieties ...

in the marketplace. Painters such as

Alexander Calder Alexander Calder (; July 22, 1898 – November 11, 1976) was an American sculptor known both for his innovative mobiles (kinetic sculptures powered by motors or air currents) that embrace chance in their aesthetic, his static "stabiles", and his ...

and

Jackson Pollock Paul Jackson Pollock (; January 28, 1912August 11, 1956) was an American painter and a major figure in the abstract expressionist movement. He was widely noticed for his " drip technique" of pouring or splashing liquid household paint onto a ho ...

are known to have employed arylide yellow in their artworks.Arylide Yellow
Colourlex

Production

The compound is obtained by

azo coupling In organic chemistry, an azo coupling is an organic reaction between a diazonium compound () and another aromatic compound that produces an azo compound (). In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the e ...

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile start ...

and acetoacetanilide or their derivatives. The class of compounds was discovered in Germany in 1909.K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. : HansaYellowPigmentsCorrected

Examples

Members of this class include: * Pigment Yellow 6 ( CAS# 2512-29-0), derived from 4-chloro-2-nitroaniline (diazonium precursor) and

(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 Pigment Yellow 16 is an organic compound that is classified as a diarylide pigment. Pigment Yellow 16 is used as a yellow colorant, and is classified as an arylide yellow. Also called permanent yellow, its color index number is 20040. The ...

derived from 2,4-dichloroaniline (diazonium precursor) and

tolidine 2-Tolidine (orthotolidine, o-tolidine; not to be confused with ''o''-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorle ...

(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.

References

Microstructural Characteristics of Paint PigmentsA Deep Technical Insight On Arylide Yellow Organic PigmentsArylide Yellow GY - Pigment Yellow 74
Industries Details {{shades of yellow Pigments Organic pigments Shades of yellow Azo dyes

Production

Examples

See also

References