Arylide yellow | |
---|---|
Color coordinates | |
Hex triplet | #E9D66B |
sRGB B (r, g, b) | (233, 214, 107) |
HSV (h, s, v) | (51°, 54%, 91%) |
CIELChuv (L, C, h) | (85, 71, 76°) |
Source | |
ISCC–NBS descriptor | Brilliant greenish yellow |
B: Normalized to [0–255] (byte) |
Arylide yellow, also known as Hansa yellow and monoazo yellow, is 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, acrylics and watercolors. 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 in the marketplace. Painters such as Alexander Calder and Jackson Pollock are known to have employed arylide yellow in their artworks. [1]
The compound is obtained by azo coupling of aniline and acetoacetanilide or their derivatives. The class of compounds was discovered in Germany in 1909. The initially formed diazo compound tautomerizes to give a ketohydrazone, which features extended pi-conjugation. [2]
Members of this class include:
Several monoazo yellows are used as artists' pigments, frequently marketed under the names 'Hansa' or Arylide. [3] These include:
Aniline is an organic compound with the formula C6H5NH2. 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 starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Oil paint is a type of slow-drying paint that consists of particles of pigment suspended in a drying oil, commonly linseed oil. Oil paint also has practical advantages over other paints, mainly because it is waterproof.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.
Azo compounds are organic compounds bearing the functional group diazenyl.
Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, artists' watercolor paints, and color laser printer toner. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the alizarin dyes.
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X− where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.
In organic chemistry, an azo coupling is an 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 electrophile, and the activated carbon, serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate.
3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes.
2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2. It is mainly used as a precursor to o-phenylenediamine.
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.
Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorless liquid.
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. Being pigments, these compounds exist as (yellow) powders of low solubility in water. They are similar to the simpler monoazo pigments called arylide yellows.
Pigment Yellow 16 is an organic compound that is classified as a diarylide pigment.
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. This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows, one example being Pigment Yellow 74.
The Sepung Bridge is the first curved, cable-stayed bridge in South Korea. It crosses the Gwangyang western river, a railway and a roadway in South Korea. It was built by Iksan Regional Construction & Management Administration.
1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.
Naphtholactam is an organic compound derived from naphthalene. It is a tricyclic species consisting of a naphthalene core fused with a lactam (NH-CO-) at the 1,8-positions. The N-alkyl derivatives are commercially important.
Pigment Yellow 74 is an azo dye and classified as an arylide yellow. It is an intensely yellow-green solid. It is prepared by azo coupling of the diazonium derivative of 2-methoxy-4-nitroaniline with 2-methoxyacetoacetanilide. It is a flat molecule, enforced by the hydrogen-bonding via the ketohydrazide group.
Pigment Yellow 97 is widely used as a yellow colorant, and is classified as an arylide yellow. It is distinguished by the presence of a sulfonylaminophenyl group, which renders the material particularly insoluble. It is derived from two fairly complicated precursors. The acetoacetanilide component is made from 2,5-dimethoxy-4-chloroaniline. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent.he compound is obtained via acetoacetylation of o-tolidine using diketene. The resulting bisacetoacetylated compound is coupled with two equiv of the diazonium salt obtained from 2,4-dichloroaniline. Although it is often depicted as an azo compound, X-ray crystallography shows that the molecule exists as a hydrazone.
Pigment Yellow 3 is a commercial colorant, sometimes classified as an arylide yellow. In terms of color and structure, it is closely related to Pigment Yellow 1, where the anilide component lacks substituents and the diazo component has methyl in place of chloro.