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A dye is a colored substance that chemically bonds to the
substrate Substrate may refer to: Physical layers *Substrate (biology), the natural environment in which an organism lives, or the surface or medium on which an organism grows or is attached ** Substrate (locomotion), the surface over which an organism lo ...
to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an
aqueous solution An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, or sodium chloride (NaCl), in water would be re ...
and may require a mordant to improve the fastness of the dye on the fiber. There are two broad categories of dyes: natural and synthetic; Natural dyes are dyes extracted from plants, Insects, or minerals. The majority of natural dyes are vegetable dyes derived from plant sources such as
roots A root is the part of a plant, generally underground, that anchors the plant body, and absorbs and stores water and nutrients. Root or roots may also refer to: Art, entertainment, and media * ''The Root'' (magazine), an online magazine focusing ...
, berries,
bark Bark may refer to: * Bark (botany), an outer layer of a woody plant such as a tree or stick * Bark (sound), a vocalization of some animals (which is commonly the dog) Places * Bark, Germany * Bark, Warmian-Masurian Voivodeship, Poland Arts, ...
,
leaves A leaf (plural, : leaves) is any of the principal appendages of a vascular plant plant stem, stem, usually borne laterally aboveground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", wh ...
, and wood, as well as other biological sources like fungi. Synthetic dyes are also referred to as "coal tar dyes" because they are derived from substances that, until recently, could only be extracted from coal tar. A synthetic dye consists of a
chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...
and an
auxochrome An auxochrome (from Ancient Greek ''auxanō'' "increase" and ''chrōma'' "colour") is a group of atoms attached to a chromophore which modifies the ability of that chromophore to absorb light. They themselves fail to produce the colour; but whe ...
added to a benzene derivative. Both dyes and pigments are colored, because they absorb only some wavelengths of visible light. Dyes are usually soluble in water, whereas pigments are insoluble. Some dyes can be rendered insoluble with the addition of salt to produce a lake pigment.


History

Textile dyeing dates back to the Neolithic period. Throughout history, people have dyed their textiles using common, locally available materials. Scarce dyestuffs that produced brilliant and permanent colors such as the natural invertebrate dyes Tyrian purple and crimson kermes were highly prized luxury items in the ancient and medieval world. Plant-based dyes such as woad, indigo, saffron, and
madder ''Rubia'' is the type genus of the Rubiaceae family of flowering plants, which also contains coffee. It contains around 80 species of perennial scrambling or climbing herbs and subshrubs native to the Old World. The genus and its best-known spe ...
were important trade goods in the economies of Asia and Europe. Across Asia and Africa, patterned fabrics were produced using resist dyeing techniques to control the absorption of color in piece-dyed cloth. Dyes from the New World such as cochineal and
logwood ''Haematoxylum campechianum'' (blackwood, bloodwood tree, bluewood, campeachy tree, campeachy wood, campeche logwood, campeche wood, Jamaica wood, logwood or logwood tree) is a species of flowering tree in the legume family, Fabaceae, that is na ...
were brought to Europe by the Spanish treasure fleets, and the dyestuffs of Europe were carried by colonists to America. Dyed
flax Flax, also known as common flax or linseed, is a flowering plant, ''Linum usitatissimum'', in the family Linaceae. It is cultivated as a food and fiber crop in regions of the world with temperate climates. Textiles made from flax are known in ...
fibers have been found in the
Republic of Georgia A republic () is a "state in which power rests with the people or their representatives; specifically a state without a monarchy" and also a "government, or system of government, of such a state." Previously, especially in the 17th and 18th c ...
in a prehistoric cave dated to 36,000 BP.
Archaeological Archaeology or archeology is the scientific study of human activity through the recovery and analysis of material culture. The archaeological record consists of artifacts, architecture, biofacts or ecofacts, sites, and cultural landscap ...
evidence shows that, particularly in India and Phoenicia, dyeing has been widely carried out for over 5,000 years. Early dyes were obtained from animal, vegetable or mineral sources, with no to very little processing. By far the greatest source of dyes has been from the plant kingdom, notably roots, berries, bark, leaves and wood, only few of which are used on a commercial scale.


Natural and synthetic

The majority of natural dyes are derived from non-animal sources: roots, berries, bark, leaves, wood, fungi and
lichen A lichen ( , ) is a composite organism that arises from algae or cyanobacteria living among filaments of multiple fungi species in a mutualistic relationship.J. Pullar and Sons J. Pullar and Sons Ltd. (also known as J. & J. Pullar and Pullars of Perth) was a dyeworks based in Perth, Scotland. It was founded by John Pullar in 1824 in Perth's Little Pomarium district and pioneered the first synthetic dyes. ''Pullars of P ...
in Scotland.John Pullar (1803–1878)
- ''The Courier & Advertiser'', 7 June 2016
Other than pigmentation, they have a range of applications including
organic dye laser Organic lasers use an organic (carbon based) material as the gain medium. The first organic laser was the liquid dye laser. These lasers use laser dye solutions as their gain media. Organic lasers are inherently tunable and when configured as ...
s, optical media ( CD-R) and
camera sensors An image sensor or imager is a sensor that detects and conveys information used to make an image. It does so by converting the variable attenuation of light waves (as they refraction, pass through or reflection (physics), reflect off objects) in ...
( color filter array). The first synthetic dye, mauve, was discovered serendipitously by William Henry Perkin in 1856. The discovery of mauveine started a surge in synthetic dyes and in organic chemistry in general. Other aniline dyes followed, such as
fuchsine Fuchsine (sometimes spelled fuchsin) or rosaniline hydrochloride is a magenta dye with chemical formula C20H19N3·HCl.
,
safranine Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospo ...
, and
induline Induline is a dye of blue, bluish-red or black shades. Induline consists of a mixture of several intensely colored species, so the name is often indulines. It was one of the first synthetic dyes, discovered in 1863 by J. Dale and Heinrich Caro. The ...
. Many thousands of synthetic dyes have since been prepared.


Synthetic dyes

The discovery of mauve also led to developments within immunology and chemotherapy. In 1863 the forerunner to Bayer AG was formed in what became Wuppertal, Germany. In 1891, Paul Ehrlich discovered that certain cells or organisms took up certain dyes selectively. He then reasoned that a sufficiently large dose could be injected to kill pathogenic microorganisms, if the dye did not affect other cells. Ehrlich went on to use a compound to target
syphilis Syphilis () is a sexually transmitted infection caused by the bacterium ''Treponema pallidum'' subspecies ''pallidum''. The signs and symptoms of syphilis vary depending in which of the four stages it presents (primary, secondary, latent, an ...
, the first time a chemical was used in order to selectively kill bacteria in the body. He also used
methylene blue Methylthioninium chloride, commonly called methylene blue, is a salt used as a dye and as a medication. Methylene blue is a thiazine dye. As a medication, it is mainly used to treat methemoglobinemia by converting the ferric iron in hemoglobin ...
to target the plasmodium responsible for malaria.


Chemistry

The color of a dye is dependent upon the ability of the substance to absorb light within the visible region of the electromagnetic spectrum (380-750 nm). An earlier theory known as Witt theory stated that a colored dye had two components, a
chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...
which imparts color by absorbing light in the visible region (some examples are
nitro Nitro may refer to: Chemistry *Nitrogen, a chemical element and a gas except at very low temperatures, with which many compounds are formed: **Nitro compound, an organic compound containing one or more nitro functional groups, -NO2 **Nitroalkene, ...
, azo, quinoid groups) and an
auxochrome An auxochrome (from Ancient Greek ''auxanō'' "increase" and ''chrōma'' "colour") is a group of atoms attached to a chromophore which modifies the ability of that chromophore to absorb light. They themselves fail to produce the colour; but whe ...
which serves to deepen the color. This theory has been superseded by modern electronic structure theory which states that the color in dyes is due to excitation of valence
π-electron In chemistry, pi bonds (π bonds) are covalent chemical bonds, in each of which two lobes of an orbital on one atom overlap with two lobes of an orbital on another atom, and in which this overlap occurs laterally. Each of these atomic orbitals ...
s by visible light.


Types

Dyes are classified according to their solubility and chemical properties. Acid dyes are water- soluble anionic dyes that are applied to fibers such as silk, wool, nylon and modified acrylic fibers using neutral to acid dye baths. Attachment to the fiber is attributed, at least partly, to salt formation between anionic groups in the dyes and cationic groups in the fiber. Acid dyes are not substantive to
cellulosic Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wa ...
fibers. Most synthetic food colors fall in this category. Examples of acid dye are Alizarine Pure Blue B,
Acid red 88 Acid red 88 is an azo dye. Due to its intense colour, solid samples appear almost black. It is used to dye cotton textiles red. A closely related acid dye is Acid Red 13. Preparation and use It can be obtained by azo coupling of naphthionic aci ...
, etc. Basic dyes are water-soluble cationic dyes that are mainly applied to acrylic fibers, but find some use for wool and silk. Usually
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
is added to the dye bath to help the uptake of the dye onto the fiber. Basic dyes are also used in the coloration of paper. Direct or substantive dyeing is normally carried out in a neutral or slightly
alkaline In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a base (chemistry), basic, ionic compound, ionic salt (chemistry), salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as ...
dye bath, at or near
boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envir ...
, with the addition of either
sodium chloride Sodium chloride , commonly known as salt (although sea salt also contains other chemical salts), is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. With molar masses of 22.99 and 35.45 g ...
(NaCl) or
sodium sulfate Sodium sulfate (also known as sodium sulphate or sulfate of soda) is the inorganic compound with formula Na2SO4 as well as several related hydrates. All forms are white solids that are highly soluble in water. With an annual production of 6 milli ...
(Na2SO4) or
sodium carbonate Sodium carbonate, , (also known as washing soda, soda ash and soda crystals) is the inorganic compound with the formula Na2CO3 and its various hydrates. All forms are white, odourless, water-soluble salts that yield moderately alkaline solutions ...
(Na2CO3). Direct dyes are used on cotton, paper, leather, wool, silk and nylon. They are also used as pH indicators and as biological stains.
Mordant dye A mordant or dye fixative is a substance used to set (i.e. bind) dyes on fabrics by forming a coordination complex with the dye, which then attaches to the fabric (or tissue). It may be used for dyeing fabrics or for intensifying stains in ...
s require a mordant, which improves the fastness of the dye against water, light and perspiration. The choice of mordant is very important as different mordants can change the final color significantly. Most natural dyes are mordant dyes and there is therefore a large literature base describing dyeing techniques. The most important mordant dyes are the synthetic mordant dyes, or chrome dyes, used for wool; these comprise some 30% of dyes used for wool, and are especially useful for black and navy shades. The mordant potassium dichromate is applied as an after-treatment. It is important to note that many mordants, particularly those in the heavy metal category, can be hazardous to health and extreme care must be taken in using them. Vat dyes are essentially insoluble in water and incapable of dyeing fibres directly. However, reduction in
alkaline liquor A lye is a metal hydroxide traditionally obtained by leaching wood ashes, or a strong alkali which is highly soluble in water producing caustic basic solutions. "Lye" most commonly refers to sodium hydroxide (NaOH), but historically has been us ...
produces the water-soluble
alkali In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a basic, ionic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a ...
metal salt of the dye. This form is often colorless, in which case it is referred to as a
Leuco dye A leuco dye (from the Greek λευκός ''leukos'': white ) is a dye which can switch between two chemical forms; one of which is colorless. Reversible transformations can be caused by heat, light or pH; resulting in examples of thermochromism, ...
, and has an affinity for the textile fibre. Subsequent oxidation reforms the original insoluble dye. The color of denim is due to indigo, the original vat dye. Reactive dyes utilize a
chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...
attached to a
substituent A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...
that is capable of directly reacting with the fiber substrate. The covalent bonds that attach reactive dye to natural fibers make them among the most permanent of dyes. "Cold" reactive dyes, such as
Procion MX Procion is a brand of fibre reactive dyes. They are commonly used in tie dye and other textile crafts. They are dichlorotriazine dyes and were originally made by Imperial Chemical Industries. The brand name is now owned by Dystar, but, since the ...
, Cibacron F, and Drimarene K, are very easy to use because the dye can be applied at room temperature. Reactive dyes are by far the best choice for dyeing cotton and other cellulose fibers at home or in the art studio. Disperse dyes were originally developed for the dyeing of cellulose acetate, and are water-insoluble. The dyes are finely ground in the presence of a dispersing agent and sold as a paste, or spray-dried and sold as a powder. Their main use is to dye
polyester Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...
, but they can also be used to dye nylon,
cellulose triacetate Cellulose triacetate, (triacetate, CTA or TAC) is a chemical compound produced from cellulose and a source of acetate esters, typically acetic anhydride. Triacetate is commonly used for the creation of fibres and film base. It is chemically si ...
, and acrylic fibers. In some cases, a dyeing temperature of is required, and a pressurized dyebath is used. The very fine particle size gives a large surface area that aids dissolution to allow uptake by the fiber. The dyeing rate can be significantly influenced by the choice of dispersing agent used during the grinding. Azoic dyeing is a technique in which an insoluble
Azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N ...
is produced directly onto or within the fiber. This is achieved by treating a fiber with both diazoic and coupling
components Circuit Component may refer to: •Are devices that perform functions when they are connected in a circuit.   In engineering, science, and technology Generic systems * System components, an entity with discrete structure, such as an assem ...
. With suitable adjustment of dyebath conditions the two components react to produce the required insoluble azo dye. This technique of dyeing is unique, in that the final color is controlled by the choice of the diazoic and coupling components. This method of dyeing cotton is declining in importance due to the toxic nature of the chemicals used. Sulfur dyes are inexpensive dyes used to dye cotton with dark colors. Dyeing is effected by heating the fabric in a solution of an organic compound, typically a nitrophenol derivative, and sulfide or polysulfide. The organic compound reacts with the sulfide source to form dark colors that adhere to the fabric. Sulfur Black 1, the largest selling dye by volume, does not have a well defined chemical structure. Some dyes commonly used in Staining:


Food dyes

One other class that describes the role of dyes, rather than their mode of use, is the food dye. Because food dyes are classed as
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salt ...
s, they are manufactured to a higher standard than some industrial dyes. Food dyes can be direct, mordant and vat dyes, and their use is strictly controlled by legislation. Many are azo dyes, although anthraquinone and triphenylmethane compounds are used for colors such as green and blue. Some naturally occurring dyes are also used.


Other important dyes

A number of other classes have also been established, including: * Oxidation bases, for mainly hair and fur * Laser dyes: rhodamine 6G and coumarin dyes. * Leather dyes, for leather *
Fluorescent brightener Optical brighteners, optical brightening agents (OBAs), fluorescent brightening agents (FBAs), or fluorescent whitening agents (FWAs), are chemical compounds that absorb light in the ultraviolet and violet region (usually 340-370 nm) of the ...
s, for textile fibres and paper *
Solvent dye A solvent dye is a dye soluble in organic solvents. It is usually used as a solution in an organic solvent. Solvent dyes are used to color organic solvents, hydrocarbon fuels, waxes, lubricants, plastics, and other hydrocarbon-based nonpolar mat ...
s, for wood staining and producing colored lacquers, solvent inks, coloring oils, waxes. * Contrast dyes, injected for magnetic resonance imaging, are essentially the same as clothing dye except they are coupled to an agent that has strong paramagnetic properties. * Mayhems dye, used in water cooling for looks, often rebranded RIT dye


Chromophoric dyes

By the nature of their
chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...
, dyes are divided into: * :Acridine dyes, derivates of acridine * :Anthraquinone dyes, derivates of anthraquinone * Arylmethane dyes ** :Diarylmethane dyes, based on diphenyl methane ** :Triarylmethane dyes, derivates of triphenylmethane * :Azo dyes, based on -N=N- azo structure * Phthalocyanine dyes, derivatives of phthalocyanine * Quinone-imine dyes, derivatives of
quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds
uch as benzene or naphthalene Uch ( pa, ; ur, ), frequently referred to as Uch Sharīf ( pa, ; ur, ; ''"Noble Uch"''), is a historic city in the southern part of Pakistan's Punjab province. Uch may have been founded as Alexandria on the Indus, a town founded by Alexand ...
by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double ...
** :Azin dyes *** :Eurhodin dyes *** Safranih ***
dyes A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and ...
, derivates of
safranin Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospo ...
** Indamins ** :Indophenol dyes, derivates of indophenol ** :Oxazin dyes, derivates of oxazin ** Oxazone dyes, derivates of oxazone ** :Thiazine dyes * :Thiazole dyes * :Safranin dyes * Xanthene dyes ** Fluorene dyes, derivatives of
fluorene Fluorene , or 9''H''-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial pu ...
*** Pyronin dyes ** :Fluorone dyes, based on fluorone *** :Rhodamine dyes, derivatives of rhodamine


Pollution

Dyes produced by the textile, printing and paper industries are a source of pollution of rivers and waterways. An estimated 700,000 tons of dyestuffs are produced annually (1990 data). The disposal of that material has received much attention, using chemical and biological means.


Classical dyes and their use in medicine and laboratory

According to the
Merriam-Webster Merriam-Webster, Inc. is an American company that publishes reference books and is especially known for its dictionaries. It is the oldest dictionary publisher in the United States. In 1831, George and Charles Merriam founded the company as ...
dictionary, a dye or stain is one that is capable of penetrating living cells or tissues without causing immediate visible degenerative changes; thus, it is also referred to as a vital stain. Supravital staining entails the removal of living cells from an organism, whereas intravital staining entails the injection (or other administration) of the dye into the organism. The term "vital stain" is occasionally used interchangeably with an intravital stain and, in some instances, with a supravital stain, the underlying concept being that the cell being examined is still alive. In a stricter sense, the term "vital staining" means the polar opposite of "supravital staining." If living cells absorb the stain during supravital staining, they exclude it during "vital staining"; for example, they color negatively while only dead cells color positively, and thus viability can be determined by counting the percentage of total cells that stain negatively. Because the dye determines whether the staining is supravital or intravital, a combination of supravital and vital dyes can be used to more accurately classify cells into various groups (e.g., viable, dead, dying) .https://www.intechopen.com/online-first/78967


See also

* Biological pigment, any colored substance in organisms * Blue Wool Scale * Hair coloring *
Industrial dye degradation Industrial dye degradation is any of a number of processed by which dyes are broken down, ideally into innocuous products. Many dyes, specifically in the textile industry such as methylene blue or methyl red, are released into ecosystems through ...
*
J-aggregate A J-aggregate is a type of dye with an absorption band that shifts to a longer wavelength (bathochromic shift) of increasing sharpness (higher absorption coefficient) when it aggregates under the influence of a solvent or additive or concentration ...
* Laser dyes *
List of dyes This is a list of dyes with Colour Index International generic names and numbers and CAS Registry Number, CAS Registry numbers. Note * Synonyms should be treated with caution because they are often used inconsistently, see Talk:List_of_dyes, dis ...
* Oxidant *
Phototendering Phototendering is the process by which organic fibres and textiles lose strength and flexibility as a result of exposure to sunlight. It is the ultraviolet component of the sun's spectrum which affects fibres, causing chain degradation and hence lo ...
*
Stain A stain is a discoloration that can be clearly distinguished from the surface, material, or medium it is found upon. They are caused by the chemical or physical interaction of two dissimilar materials. Accidental staining may make materials app ...
* Natural dyes * Pigments ** Inorganic pigments **
Organic pigments Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...


References


Further reading

* Abelshauser, Werner. ''German History and Global Enterprise: BASF: The History of a Company'' (2004) covers 1865 to 2000 * Beer, John J. ''The Emergence of the German Dye Industry'' (1959) {{Authority control Textile chemistry