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Indigo dye is an organic compound with a distinctive blue 2.1 Plant sources
color (see indigo). Historically, indigo was a natural dye
extracted from the leaves of certain plants, and this pro- A variety of plants have provided indigo throughout his-
cess was important economically because blue dyes were tory, but most natural indigo was obtained from those in
once rare. A large percentage of indigo dye produced to- the genus Indigofera, which are native to the tropics. The
day several thousand tons each year is synthetic. It is primary commercial indigo species in Asia was true in-
the blue often associated with blue jeans. digo (Indigofera tinctoria, also known as I. sumatrana).
A common alternative used in the relatively colder sub-
tropical locations such as Japans Ryukyu Islands and Tai-
wan is Strobilanthes cusia. Dyers knotweed (Polygonum
1 Uses tinctorum) was the most important blue dye in East Asia
until the arrival of the Indigofera species from the south,
which yield more dye. In Central and South America, the
species grown is I. suruticosa (ail). In Europe woad
containing the same dye was used for blue-dying. Sev-
eral plants contain indigo, but low concentrations make
them dicult to work with and the color is then more
easily tainted by other dye substances, typically leading
to a greenish tinge.
Natural sources also include mollusks, the Murex sea
snails produce a mixture of indigo and dibromoindigo
(red) which together produce a range of purple hues
known as Tyrian purple. Light exposure during part of
the dying process can convert the dibromoindigo into in-
digo resulting in blue hues known as royal blue or hyacinth
purple.
2.2 Extraction
The precursor to indigo is indican, a colorless, water-
soluble derivative of the amino acid tryptophan. Indican
Indigo dye readily hydrolyzes to release -D-glucose and indoxyl.
Oxidation by exposure to air converts indoxyl to indigo.
Indican was obtained from the processing of the plants
The primary use for indigo is as a dye for cotton yarn,
leaves, which contain as much as 0.20.8% of this com-
which is mainly for the production of denim cloth for blue
pound. The leaves were soaked in water and fermented
jeans. On average, a pair of blue jean trousers requires
to convert the glycoside indican present in the plant to
312 g of indigo. Small amounts are used for dyeing wool
the blue dye indigotin.[2] The precipitate from the fer-
and silk.
mented leaf solution was mixed with a strong base such as
Indigo carmine, or indigo, is an indigo derivative which lye, pressed into cakes, dried, and powdered. The powder
is also used as a colorant. About 20 thousand tons are was then mixed with various other substances to produce
produced annually, again mainly for blue jeans.[1] It is dierent shades of blue and purple.
also used as a food colorant, and is listed in the United
States as FD&C Blue No. 2.
3 History of natural indigo
Indigo was used in India, which was also the earliest ma-
2 Natural indigoes jor center for its production and processing.[3] The I. tinc-
toria species was domesticated in India.[3] Indigo, used as
1
2 3 HISTORY OF NATURAL INDIGO
named, in his revised account of the rainbow in Lectiones sis of indigo remained impractical, so the search for alter-
Opticae of 1675.[6] native starting materials at BASF and Hoechst continued.
[13]
In North America indigo was introduced into colonial Johannes Peger and Karl Heumann eventually [14]
came
South Carolina by Eliza Lucas Pinckney, where it be- up with industrial mass production synthesis. The syn-
came the colonys second-most important cash crop (after thesis of N-(2-carboxyphenyl)glycine from the easy to
[7]
rice). As a major export crop, indigo supported plan- obtain aniline provided a new and economically attractive
tation slavery there.[8] When Benjamin Franklin sailed to route. BASF developed a commercially feasible man-
France in November 1776 to enlist Frances support for ufacturing process that was in use by 1897. In 2002,
17,000 tons of synthetic indigo were produced world-
the American Revolutionary War, 35 barrels of indigo
were on board the Reprisal, the sale of which would help wide.
fund the war eort.[9] In colonial North America, three
commercially important species are found: the native I. 4.1 Developments in dyeing technology
caroliniana, and the introduced I. tinctoria and I. suru-
ticosa.[10]
Because of its high value as a trading commodity, indigo
was often referred to as blue gold.[11]
Peasants in Bengal revolted against unfair treatment by
the East India Company traders/planters in what became
known as the Indigo revolt in 1859, during the British
Raj of India. The play Nil Darpan by Dinabandhu Mitra
is based on the slavery and forced cultivation of indigo.
The demand for indigo in the 19th century is indicated
by the fact that in 1897, 7,000 km2 (2,700 sq mi)
were dedicated to the cultivation of indican-producing Indigo white (leuco-indigo)
plants, mainly in India. By comparison, the country of
Luxembourg is 2,586 km2 (998 sq mi).[1]
4.1.1 Indigo white
4.1.2 Direct printing Indigo is a dark blue crystalline powder that sublimes
at 390392 C (734738 F). It is insoluble in water,
Two dierent methods for the direct application of in- alcohol, or ether, but soluble in DMSO, chloroform,
digo were developed in England in the 18th century and nitrobenzene, and concentrated sulfuric acid. The
remained in use well into the 19th century. The rst chemical formula of indigo is C16 H10 N2 O2 .
method, known as 'pencil blue' because it was most of- The molecule absorbs light in the orange part of the spec-
ten applied by pencil or brush, could be used to achieve trum ( = 613 nm).[16] The compound owes its deep
dark hues. Arsenic trisulde and a thickener were added color to the conjugation of the double bonds, i.e. the
to the indigo vat. The arsenic compound delayed the ox- double bonds within the molecule are adjacent and the
idation of the indigo long enough to paint the dye onto molecule is planar. In indigo white, the conjugation is
fabrics. interrupted because the molecule is nonplanar.
5
lms by vacuum evaporation.[19] [11] History of Indigo & Indigo Dyeing. wildcolours.co.uk.
Wild Colours and natural Dyes. Retrieved 30 December
2015. Indigo was often referred to as Blue Gold as it was
an ideal trading commodity; high value, compact and long
6 Safety and the environment lasting
[7] Eliza Layne Martin. Eliza Lucas Pinckney:Indigo in the [21] Denison MS, Nagy SR (2003). Activation of
Atlantic World (PDF). Retrieved 2013-08-24. the aryl hydrocarbon receptor by structurally di-
verse exogenous and endogenous chemicals.
[8] Andrea Feeser, Red, White, and Black Make Blue: Indigo Annu. Rev. Pharmacol. Toxicol. 43: 30934.
in the Fabric of Colonial South Carolina Life (University doi:10.1146/annurev.pharmtox.43.100901.135828.
of Georgia Press; 2013) PMID 12540743.
10 External links
Plant Cultures: botany, history and uses of indigo
11.2 Images
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