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Carbonyl Dyes
Carbonyl dyes are dyes which comprise at least two conjugated carbonyl groups. Both anthraquinone dyes and indigo dyes belong to the group of carbonyl dyes. The most important natural dyes - indigo, Tyrian purple, alizarin and carmine - have this partial structure. The most important synthetic carbonyl dyes are based on anthraquinone. The main advantages of carbonyl dyes are the possibility of reducing the carbonyl groups to water-soluble dienols (→Vat dyes A value-added tax (VAT), known in some countries as a goods and services tax (GST), is a type of tax that is assessed incrementally. It is levied on the price of a product or service at each stage of production, distribution, or sale to the end ...), which is advantageous in industrial applications. On the other hand, by introducing suitable electron donating groups, the absorption maximum of the resulting dyes can be shifted to almost any region of the VIS spectrum.{{citation, surname1=Heinrich Zollinger, title=Color ...
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Conjugated System
In theoretical chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented as having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele. Conjugation is the overlap of one p-orbital with another across an adjacent σ bond (in transition metals, d-orbitals can be involved). A conjugated system has a region of overlapping p-orbitals, bridging the interjacent locations that simple diagrams illustrate as not having a π bond. They allow a delocalization of π electrons across all the adjacent aligned p-orbitals. The π electrons do not belong to a single bond or atom, but rather to a group of atoms. Molecules containing conjugated syst ...
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Carbonyl Group
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). The remainder of this article concerns itself with the organic chemistry definition of carbonyl, where carbon and oxygen share a double bond. Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds: Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide. A ...
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Anthraquinone Dyes
Anthraquinone dyes are an abundant group of dyes comprising a anthraquinone unit as the shared structural element. Anthraquinone itself is colourless, but red to blue dyes are obtained by introducing electron donor groups such as hydroxy or amino groups in the 1-, 4-, 5- or 8-position. Anthraquinone dyestuffs are structurally related to indigo dyestuffs and are classified together with these in the group of carbonyl dyes. Members of this dye group can be found in natural dyes as well as in synthetic dyes. Anthraquinone dyestuffs are represented in mordant and vat, but also in reactive and disperse dyes. They are characterized by very good light fastness. Natural anthraquinone dyes One of the most important anthraquinone dyes of herbal origin is alizarin, which is extracted from the dyer's madder ( Rubia tinctorum). Alizarin is the eponym for a number of structurally related dyes that use alizarin dyes (sometimes synonymous with anthraquinone dyes). It was the first natural ...
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Indigo Dye
Indigo dye is an organic compound with a distinctive blue color. Historically, indigo was a natural dye extracted from the leaves of some plants of the ''Indigofera'' genus, in particular ''Indigofera tinctoria''; dye-bearing ''Indigofera'' plants were commonly grown and used throughout the world, in Asia in particular, as an important crop, with the production of indigo dyestuff economically important due to the previous rarity of some blue dyestuffs historically. Most indigo dye produced today is synthetic, constituting several thousand tons each year. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly. Uses The primary use for indigo is as a dye for cotton yarn, mainly used in the production of denim cloth suitable for blue jeans; on average, a pair of blue jeans requires just to of dye. Smaller quantities are used in the dyeing of wool and ...
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Indigo
Indigo is a deep color close to the color wheel blue (a primary color in the RGB color space), as well as to some variants of ultramarine, based on the ancient dye of the same name. The word "indigo" comes from the Latin word ''indicum'', meaning "Indian", as the dye was originally exported to Europe from India. It is traditionally regarded as a color in the visible spectrum, as well as one of the seven colors of the rainbow: the color between blue and violet; however, sources differ as to its actual position in the electromagnetic spectrum. The first known recorded use of indigo as a color name in English was in 1289. History ''Indigofera tinctoria'' and related species were cultivated in East Asia, Egypt, India, Bangladesh and Peru in antiquity. The earliest direct evidence for the use of indigo dates to around 4000 BC and comes from Huaca Prieta, in contemporary Peru. Pliny the Elder mentions India as the source of the dye after which it was named. It was importe ...
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Tyrian Purple
Tyrian purple ( grc, πορφύρα ''porphúra''; la, purpura), also known as Phoenician red, Phoenician purple, royal purple, imperial purple, or imperial dye, is a reddish-purple natural dye. The name Tyrian refers to Tyre, Lebanon. It is secreted by several species of predatory sea snails in the family Muricidae, rock snails originally known by the name 'Murex'. In ancient times, extracting this dye involved tens of thousands of snails and substantial labor, and as a result, the dye was highly valued. The colored compound is 6,6′-dibromoindigo. History Biological pigments were often difficult to acquire, and the details of their production were kept secret by the manufacturers. Tyrian purple is a pigment made from the mucus of several species of Murex snail. Production of Tyrian purple for use as a fabric dye began as early as 1200 BCE by the Phoenicians, and was continued by the Greeks and Romans until 1453 CE, with the fall of Constantinople. The pigment was expensiv ...
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Alizarin
Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historically it was derived from the roots of plants of the madder genus.The primary madder species from which alizarin historically has been obtained is ''Rubia tinctorum''. See also In 1869, it became the first natural dye to be produced synthetically. Alizarin is the main ingredient for the manufacture of the madder lake pigments known to painters as rose madder and alizarin crimson. Alizarin in the most common usage of the term has a deep red color, but the term is also part of the name for several related non-red dyes, such as Alizarine Cyanine Green and Alizarine Brilliant Blue. A notable use of alizarin in modern times is as a staining agent in biological research because it stains free calcium and certain calcium compounds a red or ligh ...
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Carmine
Carmine ()also called cochineal (when it is extracted from the cochineal insect), cochineal extract, crimson lake, or carmine lake is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. ''Carmine'' is also a general term for a particularly deep-red color. Etymology The English word "carmine" is derived from the French word ''carmin'' (12th century), from Medieval Latin ''carminium'', from Persian ''qirmiz'' ("crimson"), which itself derives from Middle Persian ''carmir'' ("red, crimson"). The Persian term ''carmir'' is likely cognate with Sanskrit ''krimiga'' ("insect-produced"), from ''krmi'' ("worm, insect"). The Persian word for "worm, insect" is ''kirm'', and in Iran (Persia) the red colorant carmine was extracted from the bodies of dead female insects such as ''Kermes vermilio'' and cochineal. The form of the term may also have been influen ...
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Anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite. Synthesis There are several current industrial methods to produce 9,10-anthraquinone: # The oxidation of anthracene. Chromium(VI) is the typical oxidant. # The Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for produc ...
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Vat Dye
Vat dyes are a class of dyes that are classified as such because of the method by which they are applied. Vat dyeing is a process that refers to dyeing that takes place in a bucket or vat. The original vat dye is indigo, once obtained only from plants but now often produced synthetically. Materials suited for vat dyeing Although almost all dyeing can be done in a vat, the term vat dye is used to describe a chemical class of dyes that are applied to cellulosic fibre (''i.e.'', cotton) using a redox reaction as described below. Because of the use of caustic soda, and the very high pH of the dye bath in the dyeing process, wool cannot be dyed using vat dyestuffs. This is because wool is soluble in caustic soda solutions. Instead, it is possible to dye wool at room temperatures with indigo (vat blue 1) and other low substantive vat dyes using soda ash as the alkali source with very little strength loss. Vat red 10, vat violet 13 and vat orange 1 can be applied in this manner as well. ...
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Electron Donating Group
In chemistry, electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications: *with regards to electron-transfer, electron-rich species have low ionization energy and/or are reducing agents. Tetrakis(dimethylamino)ethylene is an electron-rich alkene because, unlike ethylene, it forms isolable radical cation. In contrast, electron-poor alkene tetracyanoethylene is an electron acceptor, forming isolable anions. *with regards to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids. *with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to benzene, pyrrole is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring. Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by ...
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