Dye

A dye is a colored substance that is soluble in some solvent; by contrast pigments are insoluble or nearly so in all solvents. Because of their solubility, dyes can chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.^[1]

The majority of natural dyes are derived from non-animal sources such as roots, berries, bark, leaves, wood, fungi and lichens.^[2] However, due to large-scale demand and technological improvements, most dyes used in the modern world are synthetically produced from substances such as petrochemicals.^[3] Some are extracted from insects and/or minerals.^[4]

Synthetic dyes are produced from various chemicals. The great majority of dyes are obtained in this way because of their superior cost, optical properties (color), and resilience (fastness, mordancy).^[1] Both dyes and pigments are colored, because they absorb only some wavelengths of visible light. Dyes are usually soluble in some solvent, 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 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 were brought to Europe by the Spanish treasure fleets,^[5] and the dyestuffs of Europe were carried by colonists to America.^[6]

Dyed flax fibers have been found in the Republic of Georgia in a prehistoric cave dated to 36,000 BP.^[7]^[8] Archaeological 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.^[9]

Early industrialization was conducted by J. Pullar and Sons in Scotland.^[10] The first synthetic dye, mauve, was discovered serendipitously by William Henry Perkin in 1856.^[11]^[12]^[13] The discovery of mauveine started a surge in synthetic dyes and in organic chemistry in general. Other aniline dyes followed, such as fuchsine, safranine, and induline. Many thousands of synthetic dyes have since been prepared.^[14]^[15]

The discovery of mauveine in 1856 led to the development of a synthetic dyestuff industry. In Manchester, England, a number of people set up dyestuff manufacturing plant including Ivan Levinstein, Levinstein Ltd,^[16] Charles Dreyfus, Clayton Aniline Company,^[17] William Claus, Claus & co.^[18]

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, the first time a chemical was used in order to selectively kill bacteria in the body. He also used methylene blue to target the plasmodium responsible for malaria.^[19]

Classification of dyes

The color of a dye derives from the absorption of light within the visible region of the electromagnetic spectrum (380–750 nm). The chemical structure determines the light absorption and is therefore the basis for many classification schemes.^[1]

Classification according to chemical structure

Anthraquinone dyes

The basic structure of this group of dyes is anthraquinone. By varying the substituents, almost all colors from yellow to red and from blue to green can be obtained, with red and blue anthraquinone dyes being particularly important. Through reduction, the quinone can be converted into the corresponding water-soluble hydroquinone, allowing anthraquinone dyes to be used as vat dyes. With appropriate substituents, anthraquinone dyes can also be used as disperse dyes for dyeing synthetic fibers. Water-soluble anthraquinone dyes containing sulfonic acid groups are used as acid or reactive dyes.

Azo dyes

Azo dyes contain an azo group substituted with an aryl group or alkenyl group as their basic structural element. Azo dyes containing multiple azo groups are referred to as bisazo (also disazo), trisazo, tetrakisazo, and polyazo dyes. Aryl substituents are usually benzene or naphthalene derivatives, but may also include heteroaromatic systems such as pyrazoles or pyridones. Enolizable aliphatic groups, for example substituted anilides of acetoacetic acid, are used as alkenyl substituents.

The dyes are synthesized by diazotization of aromatic amines followed by azo coupling of the diazonium salts with electron-rich aromatics or β-dicarbonyl compounds. Azo dyes are by far the most important and extensive class of dyes and are represented in almost all application-related dye categories (→Classification according to application technology). No naturally occurring azo dyes are known. With the exception of turquoise and a brilliant green, almost all colors can be achieved using azo dyes. The azo group is sensitive to reducing agents; it is cleaved, resulting in discoloration of the dye. Some examples of different types of azo dyes (mono- and bisazo dyes / benzene, naphthalene residues / pyridone, acetoacetanilide coupling components / metal complex dyes):

Dioxazine dyes

Dioxazine dyes, also known as triphendioxazine dyes, contain triphendioxazine as their basic structure. These intensely colored, brilliant dyes exhibit good color fastness and thus combine advantages of both azo and anthraquinone dyes. Dioxazine dyes are commercially available as direct and reactive dyes.^[20]

Indigoid dyes

Indigoid dyes belong to the carbonyl dyes and are used as vat dyes. The most important representative is indigo, which was extracted from plants as a natural dye in ancient times and is still produced industrially in large quantities, particularly for dyeing jeans. Another natural dye is the ancient purple (C.I. Natural Violet 1 / Dibromindigo).

C.I. Vat Blue 1 (Indigo)
C.I. Natural Violet 1
Indirubin

Metal complex dyes

Metal complex dyes consist of complex compounds formed from a metal and one or more dye ligands containing electron donors. Copper and chromium compounds predominate, although cobalt, nickel, and iron complexes are also used to a lesser extent. The ligands are often azo dyes, methine dyes, formazans, or phthalocyanines. Metal complex dyes are characterized by excellent fastness properties.

Formazan dyes

Formazan dyes are structurally related to azo dyes. Their basic structure is triphenylformazan. They form chelate complexes with transition metals such as copper, nickel, or cobalt. Depending on the substituents, non-complexed formazans are orange to deep red, whereas metal-complex formazans are violet, blue, or green. They are synthesized by azo coupling of diazonium salts with hydrazones. Of particular commercial importance are blue tetradentate copper chelate complexes of various formazans, which are used mainly as reactive dyes for cotton:

C.I. Reactive Blue 160
C.I. Reactive Blue 235

Phthalocyanine dyes

Phthalocyanine dyes are copper or nickel metal complexes based on the phthalocyanine structure. They are structurally related to porphyrins and share the annulene element. By introducing water-soluble substituents—primarily via sulfochlorination—turquoise to brilliant green dyes can be obtained. Phthalocyanine dyes are distinguished by outstanding light fastness.

Phthalocyanine (Aza[18]annulene)
C.I. Reactive Blue 7

Methine dyes

Methine or polymethine dyes possess conjugated double bonds as their chromophoric system, with two terminal groups acting as an electron acceptor A and an electron donor D. These terminal groups, which usually contain nitrogen or oxygen atoms, may be part of a heterocycle, and the double bonds may be part of an aromatic system. If one or more methine groups are replaced by nitrogen atoms, the dyes are referred to as aza-analog methine dyes. This gives rise to different subclasses:

Cyanine dyes, in which the conjugated double bonds are flanked by a tertiary amino group and a quaternary ammonium compounds. ^[22] If two methine groups are replaced by nitrogen atoms and one terminal group is part of a heterocycle while the other is open-chain, the important diazahemicyanine dyes are formed. Example: Basic Red 22.

Styryl dyes: by insertion of a phenyl ring into the polyene backbone, these dyes contain a styrene structural element. Example: Disperse Yellow 31.

Triarylmethine dyes, also referred to in older literature as triphenylmethane dyes because they are derived from triphenylmethane, in which at least two of the aromatic rings carry electron-donating substituents. Example: Basic Green 4 (malachite green). ^[23]

C.I. Basic Red 22
C.I. Disperse Yellow 31
C.I. Basic Green 4 (malachite green)

Nitro and nitroso dyes

In nitro dyes, a nitro group is located on an aromatic ring in the ortho position relative to an electron donor, either a hydroxy (–OH) or an amino group (–NH₂). The oldest representative of this dye class is picric acid (2,4,6-trinitrophenol). Hydroxynitro dyes are no longer of commercial importance. This is a relatively small but historically significant dye class, whose representatives are characterized by high light fastness and simple production. Nitro dyes exhibit yellow to brown hues. Owing to their relatively small molecular size, an important application as disperse dyes is the dyeing of polyester fibers. They are also used as acid and pigment dyes.

The rare nitroso dyes are aromatic compounds containing a nitroso group. Nitroso dyes with a hydroxy group in the ortho position to the nitroso group are used exclusively as metal complexes. A typical representative is naphthol green B (C.I. Acid Green 1). ^[24]

Picric acid
Acid Orange 3
Disperse Yellow 42
C.I. Acid Green 1

Sulfur dyes

Sulfur dyes (sulfin dyes) are water-insoluble, macromolecular dyes that contain disulfide bridges or oligosulfide bonds between aromatic residues. They are produced by melting benzene, naphthalene, or anthracene derivatives with sulfur or polysulfides and have an ill-defined constitution. They are particularly suitable for dyeing cotton fiber. Similar to vat dyes, they are reduced to a water-soluble form (leuco compound) using caustic soda and dithionites or sodium sulfide, applied to the fiber, and then fixed in an insoluble form by oxidation. For toxicological and ecological reasons, oxidation with chromates is increasingly being replaced by low-sulfide sulfur dyes and sulfide-free reducing agents. Owing to their low production costs, sulfur dyes continue to play an important role in terms of volume. They are characterized by good wash and light fastness, although the colors are generally muted.^[25]

Classification according to application technology

While the color shade of a dye is essentially determined by its chromophore, dye properties can be modified by incorporating suitable chemical groups to enable dyeing of different substrates. This leads to a classification of dyes according to the dyeing process. This classification is also used by the Colour Index, an important standard reference in dye chemistry. The Colour Index (C.I.) indicates the dye class, color, and chemical identity. It lists more than 10,000 dyes, over 50% of which are azo dyes.^[26]

Mordant dyes

The term derives from mordant dyeing, in which suitable acid dyes are applied to mordanted fabrics, primarily wool and silk. Prior to dyeing, the fibers are treated with [chromium] , [iron] , or aluminum salts. During subsequent steaming, metal hydroxides form on the fiber. During dyeing, these hydroxides react with the (usually specialized) acid dye to form a metal complex dye. The process on the fiber corresponds to varnishing. ^[27]

When chromium salts are used, the dyes are referred to as chromium dyes. Depending on the dye type, the chromium salt—usually chromates or dichromates—may be added before, during, or after dyeing. Accordingly, pre-mordanting, post-mordanting, and single-bath chromium dyeing processes are distinguished. Chromium dyes are noted for their excellent wet fastness. However, heavy metal contamination of fibers and dyeing wastewater is a significant ecological concern.^[28]

Mordant dyes are designated as "C.I. Mordant Dyes" in the Colour Index. Examples:

C.I. Mordant Black 9
C.I. Mordant Yellow 8
C.I. Mordant Black 7
C.I. Mordant Red 60
C.I. Mordant Blue 9

Historically, in addition to chromium, iron, and aluminum salts, mordants based on ammonium vanadate, tannic acid, aluminum oxide, antimony, barium, lead, cobalt, copper, manganese, nickel, tin, and Turkish red oil were also used. Various antimony salts such as potassium antimony tartrate or antimony(III) chloride, as well as sodium silicate and sodium phosphate, and even cow dung, were employed as fixing agents. ^[29]

Direct dyes

Direct dyes (or substantive dyes) are absorbed directly from aqueous solution onto the fiber due to their high substantivity. They are particularly suitable for cellulose fibers. Binding to the fiber occurs through physical interactions, mainly Van der Waals forces. Most direct dyes belong to the azo dye group, especially polyazo dyes. In the Colour Index, they are designated as C.I. Direct Dyes. Examples:

C.I. Direct Blue 8
C.I. Direct Orange 26
C.I. Direct Yellow 9

Disperse dyes

Disperse dyes, which are almost insoluble in water, are primarily used for dyeing hydrophobic polyester and cellulose acetate. They are finely ground together with dispersing agents, enabling the molecularly dissolved dye to diffuse into the fiber during dyeing, where it forms a solid solution. This results in dyes with good wash and light fastness.

The vast majority of disperse dyes belong to the azo dye class. Disperse dyes represent a highly important group, particularly due to the widespread use and mechanical performance of polyester fibers. In 1999, the total sales volume in Western Europe amounted to 98 million euros.

According to the Colour Index, they are designated as "C.I. Disperse Dyes". Examples:

C.I. Disperse Orange 44
C.I. Disperse Blue 797
C.I. Disperse Red 177

Development or coupling dyes

In developing dyes, a practically water-insoluble dye is formed directly on the fiber by the reaction of a water-soluble coupling component (C.I. Azoic Coupling Component) with a water-soluble diazo component (C.I. Azoic Diazo Component). This dye class is mainly used for cellulose fibers and is characterized by very good wet fastness. The most important coupling component in developing dyes is Naphthol AS.

C.I. Azoic Coupling Component 2 (naphthol AS)
C.I. Azoic Coupling Component 35 (naphthol AS-LG)
C.I. Azoic Diazo Component 3 (Echt scarlet salt GG)
C.I. Azoic Diazo Component 35 (Variamin blue salt B)

Cationic dyes

Cationic dyes are cationic compounds that produce brilliant and lightfast colors, particularly on polyacrylonitrile (PAN) fibers and anionically modified polyester fibers. They form ionic bonds with negatively charged groups on the fiber. Various chromophores can be used in cationic dyes; in methine dyes, the positive charge is delocalized, in contrast to other chromophoric systems.

Although cationic dyes are designated as "C.I. Basic Dyes" in the Colour Index, the term "basic dyes" is no longer commonly used for this dye class in recent literature. ^[24]

C.I. Basic Orange 22
C.I. Basic Blue 3
C.I. Basic Blue 54
C.I. Basic Red 18

Vat dyes

Vat dyes comprise water-insoluble pigments that are converted into their soluble dihydro or leuco base form for dyeing by reduction (vatting) in alkaline solution. The anion exhibits sufficient affinity for cotton or viscose fibers, allowing absorption. The dye is subsequently reconverted to its insoluble form by oxidation, either by atmospheric oxygen or by oxidizing agents. The dye is effectively fixed at the molecular level within the fiber; this “precipitation within the fiber” results in very high wash and light fastness.^[30] Water-insoluble sulfur dyes exhibit similar behavior.

The most important vat dye is indigo. Indanthrene dyes are also of major importance.

Vat dyes are designated as "C.I. Vat Dyes" in the Colour Index. Examples:

C.I. Vat Green 11
C.I. Vat Orange 7
C.I. Vat Red 23
Flavanthron Yellow

Food colorants / Food dyes

Food colorants are used as food additives to compensate for color changes caused by processing or to meet consumer expectations. Both naturally occurring and synthetically produced colorants are employed. The use of food colorants is strictly regulated by law—within the EU by Regulation (EC) No. 1333/2008 of December 16, 2008, on food additives.^[31] Only approved additives bearing an E number may be marketed, and these must be declared on the product.^[32]

Food colorants are designated as "C.I. Food Dyes" in the Colour Index.

Because food dyes are classed as food additives, 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.^[33]

Solvent dyes

Solvent dyes, designated as "Solvent Dyes" in the Colour Index, are water-insoluble dyes that are soluble in various organic solvents such as alcohols, esters, or hydrocarbons. As a rule, solvent dye structures do not contain sulfonic acid or carboxyl groups. Exceptions include cationic dyes with an intramolecular sulfonate or carboxylate group acting as the counterion. Solvent dyes occur across various dye classes, including azo dyes, anthraquinone dyes, metal complex dyes, and phthalocyanines. They are used in lacquers (e.g., Zapon dyes for Zapon lacquers), for coloring mineral oil products (Sudan dyes), wax, inks, and transparent plastics. According to the Colour Index, they are designated as C.I. Solvent Dyes.

Examples:

Solvent Yellow 124
Solvent Red 27
Solvent Blue 35
C.I. Solvent Yellow 32
Sudan Black B
C.I. Solvent Red 8

Reactive dyes

During the dyeing process, reactive dyes form a covalent bond with functional groups of the fiber, resulting in dyes with high wet fastness. They constitute the largest group of dyes used for cellulose fibers, but are also employed for wool and polyamide in deep shades.^[34]

Chemically, reactive dyes consist of two components: a chromophore and one or more reactive groups, also referred to as reactive anchors. Two major reactive anchor systems are used:

Heterocyclic compounds, such as halogen-substituted triazines or pyrimidines. During dyeing, these react with hydroxyl groups of the fiber, eliminating halogen hydrides and forming stable covalent ether bonds:

So-called vinylsulfones, which react with nucleophilic groups of the fiber during dyeing via a Michael addition. Here as well, stable ether bonds are formed. In many vinyl sulfone dyes, the vinyl sulfone group is initially present in a protected form as a sulfuric acid semiester. Only under alkaline dyeing conditions is the vinyl sulfone group generated by elimination of sulfuric acid.

Both types of reactive anchors may be present simultaneously in a single reactive dye.

Azo dyes are by far the most common chromophores used in reactive dyes. However, other chromophoric systems, such as anthraquinone, formazan, and phthalocyanine dyes, are also important. Reactive dyes are designated as "C.I. Reactive Dyes" in the Colour Index.

Examples:

C.I. Reactive Orange 107
C.I. Reactive Blue 2
C.I. Reactive Blue 21
C.I. Reactive Red 227
C.I. Reactive Orange 1

Acid dyes

Acid dyes are hydrophilic dyes containing anionic substituents, usually sulfonic acid groups. Most acid dyes belong to the azo dye class, although other chromophores also occur. They are mainly used for dyeing wool, silk, and polyamide, with dyeing carried out in the pH range 2–6. When small dye molecules are used, uniform dyeing is achieved, with dye molecules forming primarily salt-like bonds with ammonium groups of the fiber. The wash fastness of such dyes is relatively moderate. With increasing molecular size, dye–fiber binding is enhanced through adsorption forces between the hydrophobic parts of the dye molecule and the fiber. This improves wet fastness, but often at the expense of dyeing uniformity.

Acid dyes are designated as "C.I. Acid Dyes" in the Colour Index. Examples:

C.I. Acid Black 1
C.I. Acid Yellow 36
C.I. Acid Blue 117
Acid Orange 19
C.I. Acid Blue 3 (Patent Blue V)

Functional dyes

While conventional dyes are used to modify the appearance of textiles, leather, and paper, functional dyes generally serve non-aesthetic purposes. Typical applications include indicator dyes or voltage-dependent dyes.^[35]

Special dyes can

absorb light at a specific wavelength and convert it into heat (e.g., in chemical and biochemical analysis),^[35]
re-emit absorbed light at a different wavelength (as phosphorescent biomarkers or inks, fluorescence in dye lasers, chemiluminescence in the breaking or formation of chemical bonds in biochemistry),^[35]
change the polarization direction of light (e.g., in frequency doubling or as optical switches),
induce electrical phenomena (e.g., in laser printer applications),
enable photochemical processes.

Laser dyes are used in the production of some lasers, optical media (CD-R), and camera sensors (color filter array).^[36] From an economic perspective, functional dyes are particularly important in the manufacture of CDs and DVDs. The dye molecules are embedded in the polycarbonate of the disc. The laser beam of the burner causes the dye molecules to absorb light energy and convert it into heat, leading to localized melting of the polycarbonate. This slightly altered surface structure is then detected during the reading process.^[37] Laser dyes are for example rhodamine 6G and coumarin dyes.^[38]

Vital dyes

A "vital dye" or stain is a dye capable of penetrating living cells or tissues without causing immediate visible degenerative changes.^[39] Such dyes are useful in medical and pathological fields in order to selectively color certain structures (such as cells) in order to distinguish them from surrounding tissue and thus make them more visible for study (for instance, under a microscope). As the visibility is meant to allow study of the cells or tissues, it is usually important that the dye not have other effects on the structure or function of the tissue that might impair objective observation.

A distinction is drawn between dyes that are meant to be used on cells that have been removed from the organism prior to study (supravital staining) and dyes that are used within a living body - administered by injection or other means (intravital staining) - as the latter is (for instance) subject to higher safety standards, and must typically be a chemical known to avoid causing adverse effects on any biochemistry (until cleared from the tissue), not just to the tissue being studied, or in the short term.

The term "vital stain" is occasionally used interchangeably with both intravital and supravital stains, the underlying concept in either case being that the cells examined are 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).^[40]

Other important dyes

A number of other classes have also been established, including:

Leather dyes, for leather
Fluorescent brighteners, for textile fibres and paper
Solvent dyes, 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.^[41]
Mayhems dye, used in water cooling for looks, often rebranded RIT dye

Pollution

Dyes produced by the textile, printing and paper industries are a source of pollution of rivers and waterways.^[42] 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.^[43]

References

^ ^a ^b ^c Booth, Gerald. "Dyes, General Survey". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_073. ISBN 978-3-527-30673-2.
^ Burgess, Rebecca (8 November 2017). Harvesting Color: How to Find Plants and Make Natural Dyes. Artisan Books. ISBN 9781579654252.
^ Synthetic dyes at the Encyclopædia Britannica
^ Kassinger, Ruth (2003). Dyes: from sea snails to synthetics. Twenty-First Century Books. ISBN 9780761321125.
^ Cañamares, M. V.; Leona, M. (15 August 2008). "Study of laccaic acid and other natural anthraquinone dyes by Surface-Enhanced Raman Scattering spectroscopy". In Castillejo, Marta; Moreno, Pablo; Oujja, Mohamed; et al. (eds.). Lasers in the Conservation of Artworks: Proceedings of the International Conference Lacona VII, Madrid, Spain, 17 - 21 September 2007. CRC Press. pp. 29–33. ISBN 9780203882085. Retrieved 8 November 2017 – via Google Books.
^ Adrosko, Rita J. (8 November 1971). Natural Dyes and Home Dyeing (formerly Titled: Natural Dyes in the United States). Courier Corporation. ISBN 9780486226880. Retrieved 8 November 2017 – via Google Books.
^ Balter, Michael (11 September 2009). "Clothes Make the (Hu) Man". Science. 325 (5946): 1329. doi:10.1126/science.325_1329a. PMID 19745126.
^ Kvavadze, Eliso; Bar-Yosef, Ofer; Belfer-Cohen, Anna; Boaretto, Elisabetta; Jakeli, Nino; Matskevich, Zinovi; Meshveliani, Tengiz (11 September 2009). "30,000-Year-Old Wild Flax Fibers". Science. 325 (5946): 1359. Bibcode:2009Sci...325.1359K. doi:10.1126/science.1175404. PMID 19745144.
^ Liles, J.N (1990). The Art and Craft of Natural Dyeing. University of Tennessee Press. pp. 2–4. ISBN 9780870496707.
^ "John Pullar (1803–1878)". The Courier & Advertiser. 7 June 2016.
^ Hübner, Karl (August 2006). "150 Jahre Mauvein". Chemie in unserer Zeit. 40 (4): 274–275. doi:10.1002/ciuz.200690054.
^ Travis, Anthony S. (1990). "Perkin's Mauve: Ancestor of the Organic Chemical Industry". Technology and Culture. 31 (1): 51–82. doi:10.2307/3105760. JSTOR 3105760.
^ Eiland, Murray Lee (1999). "Problems Associated with the Dissemination of Synthetic Dyes in the Oriental Carpet Industry". Icon. 5: 138–159. JSTOR 23786082.
^ Hunger, K., ed. (2003). Industrial Dyes: Chemistry, Properties, Applications. Weinheim: Wiley-VCH. doi:10.1002/3527602011. ISBN 978-3-527-30426-4.^{[page needed]}
^ Zollinger, H. (2003). Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments (3rd ed.). Wiley-VCH. ISBN 978-3-906390-23-9.^{[page needed]}
^ 1908 Stock Exchange Year-Book
^ 1908 Stock Exchange Year-Book
^ ICI Dyestuffs Division and predecessor companies archive Claus & Co. Held at University of Manchester Library
^ Burrows, Andy; Holman, John; Parsons, Andy; Pilling, Gwen; Price, Gareth (2009). Chemistry³: Introducing inorganic, organic and physical chemistry. OUP Oxford. pp. 1005–1006. ISBN 978-0-19-927789-6.
^ Klaus Hunger, ed. (2003), [[1] at Google Books Industrial Dyes: Chemistry, Properties, Applications], Weinheim: WILEY-VCH Verlag, ISBN 978-3-662-01950-4 {{citation}}: Check |url= value (help)
^ Steingruber, Elmar. "Indigo and Indigo Colorants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_149.pub2. ISBN 978-3-527-30673-2.
^ Entry on Cyanin-Farbstoffe. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ Entry on Triarylmethan-Farbstoffe. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ ^a ^b Heinrich Zollinger (2003), [[2] at Google Books Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments] (3. ed.), Weinheim: WILEY-VCH Verlag, ISBN 3-906390-23-3 {{citation}}: Check |url= value (help)
^ Entry on Schwefel-Farbstoffe. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ Kirk-Othmer, Jacqueline I. Kroschwitz: Encyclopedia of Chemical Technology. 5. Ausgabe, Vol. 9, 2005, ISBN 978-0-471-48494-3, S. 349.
^ Paul Rys, Heinrich Zollinger: Leitfaden der Farbstoffchemie. 2. Auflage, Verlag Chemie, Weinheim 1976, ISBN 3-527-25650-4, S. 181, 182.
^ Entry on Chromierungsfarbstoffe. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ Jacob Herzfeld (1900), [[3], p. 55, at Google Books Die Bleichmittel, Beizen und Farbstoffe] (Eigenschaften, Prüfung und praktische Anwendung auf Baumwolle, Wolle, Seide, Halbwolle, Halbseide, Jute, Leinen, etc.) (2 ed.), Unikum Verlag, pp. 55–96 {{citation}}: Check |url= value (help)
^ Wittko Francke, Wolfgang Walter: Lehrbuch der Organischen Chemie. S. Hirzel Verlag, Stuttgart 2004, ISBN 3-7776-1221-9, S. 684 f.
^ "Verordnung (EG) Nr. 1333/2008 vom 16. Dezember 2008 über Lebensmittelzusatzstoffe"., abgerufen am 5. August 2019.
^ "Zulassung und Verwendung von Lebensmittelzusatzstoffen". Bundesministerium für Ernährung und Landwirtschaft. Retrieved 2019-08-05.
^ Rodriguez-Amaya, Delia B (February 2016). "Natural food pigments and colorants". Current Opinion in Food Science. 7: 20–26. doi:10.1016/j.cofs.2015.08.004.
^ H. Zollinger: Chemismus der Reaktivfarbstoffe. In: Angew. Chem. 73, Nr. 4, 1961, S. 125–136, doi:10.1002/ange.19610730402.
^ ^a ^b ^c John Griffiths: Funktionelle Farbstoffe. Ein neuer Trend in der Farbstoffchemie. In: Chemie in unserer Zeit. 27, Nr. 1, 1993, S. 21–31, doi:10.1002/ciuz.19930270104.
^ Silfvast, William T. (21 July 2008). Laser Fundamentals. Cambridge University Press. ISBN 9781139855570. Retrieved 8 November 2017 – via Google Books.
^ Klaus Roth: Die Chemie der schillernden Scheiben: CD, DVD & Co. In: Chemie in unserer Zeit. 41, Nr. 4, 2007, S. 334–345, doi:10.1002/ciuz.200700428.
^ Duarte, F. J.; Hillman, L. W., eds. (1990). Dye Laser Principles. New York.{{cite book}}: CS1 maint: location missing publisher (link)
^ "Medical Definition of VITAL DYE". www.merriam-webster.com. Retrieved 2024-10-24.
^ Ionescu, Sinziana (2023-07-26). "The Use of Indocyanine Green in Colorectal Surgery". Current Topics in Colorectal Surgery. IntechOpen. doi:10.5772/intechopen.100301. ISBN 978-1-83962-335-6. This article incorporates text available under the CC BY 3.0 license.
^ "patentstorm.us". Patentstorm.us. Archived from the original on 12 June 2011. Retrieved 8 November 2017.
^ Brindley, Lewis (July 2009). "New solution for dye wastewater pollution". Chemistry World. Retrieved 2018-07-08.
^ Xu, Xiang-Rong; Li, Hua-Bin; Wang, Wen-Hua; Gu, Ji-Dong (2004). "Degradation of dyes in aqueous solutions by the Fenton process". Chemosphere. 57 (7): 595–600. Bibcode:2004Chmsp..57..595X. doi:10.1016/j.chemosphere.2004.07.030. PMID 15488921.

v t e Dyeing
Techniques	Batik Dyeing Ikat Kasuri Kalamkari Katazome Leheriya Mordant Reactive dye printing Resist Ring dyeing Rōketsuzome Shibori Tie-dye Tsutsugaki Yūzen
Types of dyes	Dyes Natural Acid Reactive Solvent Substantive Sulfur Vat Disperse Discharge Pigment
Traditional textile dyes	Armenian cochineal Black walnut Bloodroot Brazilin Cochineal Cudbear Cutch Dyewoods Fustic Gamboge Dyer's broom Henna Indigo Kermes Logwood Madder Polish cochineal Saffron Turmeric Tyrian purple Weld Woad
History	Use of saffron Traditional dyes of the Scottish Highlands
Craft dyes	Dylon Inkodye Procion Rit
Reference	Glossary of dyeing terms List of dyes

Authority control databases
International	GND
National	United States France BnF data Japan Israel
Other	Encyclopedia of Modern Ukraine Yale LUX

Dye