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. The ...
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 compo ...
s. They are primarily used as industrial colorants including
plastics
Plastics are a wide range of synthetic polymers, synthetic or semi-synthetic materials that use polymers as a main ingredient. Their Plasticity (physics), plasticity makes it possible for plastics to be Injection moulding, moulded, Extrusion, e ...
, 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 t ...
. These pigments are usually semi-transparent and range from orange-yellow to yellow-greens. Related organic pigments are the
diarylide pigment
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 ...
s. Overall, these pigments have partially displaced the toxic
cadmium yellow 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 hor ...
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 ...
of 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
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
and acetoacetanilide
Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. It and many related compounds (prepared from various aniline der ...
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. ]
:
Examples
Members of this class include:
*Pigment Yellow
A pigment is a colored material that is completely or nearly Solubility, 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 inorg ...
6 ( CAS# 2512-29-0), derived from 4-chloro-2-nitroaniline (diazonium precursor) and 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
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
(acetoacetanilide precursor) to produce medium yellows.
*Pigment Yellow 3
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 compo ...
(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 com ...
derived from 2,4-dichloroaniline Dichloroanilines are chemical compounds which consist of an aniline ring substituted with two chlorine atoms and have the molecular formula C6H5Cl2N. There are six isomers, varying in the positions of the chlorine atoms around the ring relative to ...
(diazonium precursor) and tolidine
2-Tolidine (orthotolidine, o-tolidine; not to be confused with O-Toluidine, ''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 ...
(acetoacetanilide precursor) to produce medium-yellows.
*Pigment Yellow 74
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 compo ...
(CAS# 6358-31-2), derived from 2-methoxy-4-nitroaniline (diazonium precursor) and 2-methoxyaniline (acetoacetanilide precursor) to produce greenish-yellows.
See also
*List of colors
These are the lists of colors;
* List of colors: A–F
* List of colors: G–M
* List of colors: N–Z
* List of colors (compact)
* List of colors by shade
* List of color palettes
* List of Crayola crayon colors
* List of RAL colors
* List ...
References
Microstructural Characteristics of Paint Pigments
A Deep Technical Insight On Arylide Yellow Organic Pigments
Arylide Yellow GY - Pigment Yellow 74
Industries Details
{{shades of yellow
Pigments
Organic pigments
Shades of yellow
Azo dyes