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60-424: Overalls were originally made of denim , but they can also be made of other materials such as corduroy , chino cloth , or leather . Overalls were invented in the mid to late 1890s by Grace Howard and Jacob W. Davis at Levi Strauss & Co. , but they went through an evolution to reach their modern form. Initially created to serve as protective clothing during physically demanding work, they have since also become

120-479: A bib and straps over the shoulders. In 1927, Lee's developed a "hook-less fastener" and created "button-less" overalls. Zippers replaced buttons. Soon after, suspender buttons were traded in for belt loops to attach over-the-shoulder straps. In 1920, groups of "Overalls Clubs" formed around the United States. They took overalls as their symbol to protest the rising cost of clothing, and profiteering in

180-511: A dye (particularly for silk ) for centuries. The dye was also known to ancient civilizations in Mesopotamia , Egypt , Britain , Mesoamerica , Peru , Iran , and West Africa . Indigo was also cultivated in India, which was also the earliest major center for its production and processing. The Indigofera tinctoria species was domesticated in India. Indigo, used as a dye, made its way to

240-471: A fashion garment. Many high-fashion brands have released their own spin on overalls. Today, overalls can still be found in some workplaces, while also being worn casually by all kinds of people. The exact beginnings of the wearing of overalls are unclear, but they are mentioned in literature as early as 1776 as protective working garments commonly worn by slaves. The first evidence of overalls being mass-produced are those made by Levi Strauss and Jacob Davis in

300-479: A high waist reaching to the chest and held up by adjustable shoulder braces. Historically, military "overalls" were loose garments worn in the 18th and early 19th centuries over soldiers' breeches and gaiters when on active service or in barracks. After 1823, the term was replaced by "trousers" in British Army documents, but it survives to the present day in reference to the tight-fitting garments strapped under

360-772: A major export crop, indigo supported plantation slavery there. In the May and June 1755 issues of The Gentleman's Magazine , there appeared a detailed account of the cultivation of indigo, accompanied by drawings of necessary equipment and a prospective budget for starting such an operation, authored by South Carolina planter Charles Woodmason . It later appeared as a book. By 1775, indigo production in South Carolina exceeded 1,222,000 pounds. When Benjamin Franklin sailed to France in November 1776 to enlist France's support for

420-527: A pair of blue jeans requires 3 grams (0.11 oz) to 12 grams (0.42 oz) of dye. Smaller quantities are used in the dyeing of wool and silk. Indigo carmine , also known as indigo, is an indigo derivative which is also used as a colorant. About 20,000 tonnes are produced annually, again mainly for the production of blue jeans. It is also used as a food colorant, and is listed in the United States as FD&C Blue No. 2. A variety of plants have provided indigo throughout history, but most natural indigo

480-620: A rare commodity throughout the Middle Ages. A chemically identical dye derived from the woad plant ( Isatis tinctoria ) was used instead. In the late 15th century, the Portuguese explorer Vasco da Gama discovered a sea route to India. This led to the establishment of direct trade with India, the Spice Islands , China, and Japan. Importers could now avoid the heavy duties imposed by Persian , Levantine , and Greek middlemen and

540-451: A second synthesis in 1880 (from 2-nitrobenzaldehyde ). (It was not until 1883 that Baeyer finally determined the structure of indigo. ) The synthesis of indigo remained impractical, so the search for alternative starting materials at Badische Anilin- und Soda-Fabrik (BASF) and Hoechst continued. Johannes Pfleger and Karl Heumann eventually came up with industrial mass production synthesis. The synthesis of N-(2-carboxyphenyl)glycine from

600-434: A sheet in the same order in which they will be woven; because of this, uneven dye circulation in the bath can lead to side-to-side color variations in the woven cloth. Rope dyeing eliminates this possibility because color variations can be evenly distributed across the warp during beaming. Denim fabric dyeing is divided into two categories: indigo dyeing (Indigo dye is a unique shade of blue) and sulfur dyeing (Sulfur dye

660-498: A skein dyeing process, in which individual skeins of yarn were dipped into dye baths. Rope dyeing machines were developed in 1915, and slasher or sheet dyeing machines were developed in the 1970s. These methods involve a series of rollers that feed continuous yarns in and out of dye vats. In rope dyeing, continuous yarns are gathered together into long ropes or groups of yarns – after these bundles are dyed, they must be re-beamed for weaving. In sheet dyeing, parallel yarns are laid out as

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720-492: A vat was decorated with the techniques of shibori ( tie-dye ), kasuri , katazome , and tsutsugaki . Examples of clothing and banners dyed with these techniques can be seen in the works of Hokusai and other artists. Two different methods for the direct application of indigo were developed in England in the 18th century and remained in use well into the 19th century. The first method, known as 'pencil blue' because it

780-405: Is synthetic , constituting around 80,000 tonnes each year, as of 2023. 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. 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,

840-472: Is a dark blue crystalline powder that sublimes at 390–392 °C (734–738 °F). It is insoluble in water, alcohol , or ether , but soluble in DMSO , chloroform , nitrobenzene , and concentrated sulfuric acid . The chemical formula of indigo is C 16 H 10 N 2 O 2 . The molecule absorbs light in the orange part of the spectrum ( λ max =613 nm). The compound owes its deep color to

900-454: Is a synthetic organic dye and it is formed by sulphurisation of organic intermediates, this contains nitro or amino groups). Indigo dyeing produces the traditional blue color or shades similar to it. Sulfur dyeing produces specialty black and other colors, such as red, pink, purple, grey, rust, mustard, and green. Most denim made today is made on a shuttleless loom that produces bolts of fabric 60 inches (1,500 mm) or wider, but some denim

960-558: Is an organic compound with a distinctive blue color . Indigo is 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, particularly in Asia, with the production of indigo dyestuff economically important due to the historical rarity of other blue dyestuffs. Most indigo dye produced today

1020-405: Is available in a range of colors, but the most common denim is indigo denim in which the warp thread is dyed while the weft thread is left white. As a result of the warp-faced twill weaving, one side of the textile is dominated by the blue warp threads, and the other side is dominated by the white weft threads. Jeans fabricated from this cloth are thus predominantly white on the inside. Denim

1080-458: Is created through generally the same process: Traditional denim yarn is composed entirely of cotton . Once cotton fibers are cleaned and combed into long, cohesive lengths of similar-length fiber, they are spun into yarn using an industrial machine. Throughout the creation of denim, washes, dyes, or treatments are used to change the appearance of denim products. Some yarns may substitute an elastic component such as spandex for up to 3% of

1140-529: Is credited to Pfleger in 1901. In this process, N -phenylglycine is treated with a molten mixture of sodium hydroxide , potassium hydroxide , and sodamide . This highly sensitive melt produces indoxyl , which is subsequently oxidized in air to form indigo. Variations of this method are still in use today. An alternative and also viable route to indigo is credited to Heumann in 1897. It involves heating N -(2-carboxyphenyl)glycine to 200 °C (392 °F) in an inert atmosphere with sodium hydroxide. The process

1200-655: Is easier than the Pfleger method, but the precursors are more expensive. Indoxyl-2-carboxylic acid is generated. This material readily decarboxylates to give indoxyl, which oxidizes in air to form indigo. The preparation of indigo dye is practised in college laboratory classes according to the original Baeyer-Drewsen route. The oldest known fabric dyed indigo, dated to 6,000 years ago, was discovered in Huaca Prieta , Peru. Many Asian countries, such as India , China, Japan, and Southeast Asian nations have used indigo as

1260-670: Is not soluble in water. To be dissolved, it must undergo a chemical change ( reduction ). Reduction converts indigo into "white indigo" ( leuco -indigo). When a submerged fabric is removed from the dyebath, the white indigo quickly combines with oxygen in the air and reverts to the insoluble, intensely colored indigo. When it first became widely available in Europe in the 16th century, European dyers and printers struggled with indigo because of this distinctive property. It also required several chemical manipulations, some involving toxic materials, and presented many opportunities to injure workers. In

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1320-528: Is secreted by a common Mediterranean snail. It was highly prized in antiquity. In 1909, its structure was shown to be 6,6'-dibromoindigo (red). 6-bromoindigo (purple) is a component as well. It has never been produced on a commercial basis. The related Ciba blue (5,7,5',7'-tetrabromoindigo) is, however, of commercial value. Indigo and its derivatives featuring intra- and intermolecular hydrogen bonding have very low solubility in organic solvents. They can be made soluble using transient protecting groups such as

1380-613: Is still woven on the traditional shuttle loom , which typically produces a bolt 30 inches (760 mm) wide. Shuttle-loom-woven denim is usually recognizable by its selvedge (or selvage ), the edge of a fabric created as a continuous cross-yarn (the weft ) reverses direction at the edge side of the shuttle loom. The selvedge is traditionally accentuated with warp threads of one or more contrasting colors, which can serve as an identifying mark. Although quality denim can be made on either loom, selvedge denim has come to be associated with premium products since final production that showcases

1440-499: Is used to create a wide variety of garments, accessories, and furniture. Denim originated as a contraction of the French phrase serge de Nîmes (' serge from Nîmes '). Denim has been used in the United States since the mid-19th century. Denim initially gained popularity in 1873 when Jacob W. Davis , a tailor from Nevada , manufactured the first pair of rivet-reinforced denim pants. The popularity of denim jeans outstripped

1500-661: The Murex genus of sea snails produces a mixture of indigo and 6,6'-dibromoindigo (red), which together produce a range of purple hues known as Tyrian purple . Light exposure during part of the dyeing process can convert the dibromoindigo into indigo, resulting in blue hues known as royal blue, hyacinth purple, or tekhelet . Given its economic importance, indigo has been prepared by many methods. The Baeyer–Drewsen indigo synthesis dates back to 1882. It involves an aldol condensation of o-nitrobenzaldehyde with acetone, followed by cyclization and oxidative dimerization to indigo. This route

1560-646: The American Revolutionary War , 35 barrels of indigo were on board the Reprisal , the sale of which would help fund the war effort. In colonial North America, three commercially important species are found: the native I. caroliniana , and the introduced I. tinctoria and I. suffruticosa . In 1865 the German chemist Adolf von Baeyer began working on the synthesis of indigo. He described his first synthesis of indigo in 1878 (from isatin ) and

1620-458: The Edo period . This was due to a growing textiles industry, and because commoners had been banned from wearing silk, leading to the increasing cultivation of cotton, and consequently indigo – one of the few substances that could dye it. In North America, indigo was introduced into colonial South Carolina by Eliza Lucas , where it became the colony's second-most important cash crop (after rice). As

1680-532: The Greeks and the Romans , where it was valued as a luxury product. In Mesopotamia, a neo-Babylonian cuneiform tablet of the seventh century BC gives a recipe for the dyeing of wool, where lapis -colored wool ( uqnatu ) is produced by repeated immersion and airing of the cloth. Indigo was most probably imported from India. The Romans used indigo as a pigment for painting and for medicinal and cosmetic purposes. It

1740-566: The Indigo revolt in 1859. The Bengali play Nil Darpan by Indian playwright Dinabandhu Mitra was a fictionalized retelling of the revolt. The demand for indigo in the 19th century is indicated by the fact that in 1897, 7,000 km (2,700 sq mi) were dedicated to the cultivation of indican-producing plants, mainly in India . By comparison, the country of Luxembourg is 2,586 km (998 sq mi). In Europe, indigo remained

1800-580: The Mandinka of Mali particularly well known for their expertise. Among the Hausa male dyers, working at communal dye pits was the basis of the wealth of the ancient city of Kano , and they can still be seen plying their trade today at the same pits. The Tuareg are sometimes called the "Blue People" because the indigo pigment in the cloth of their traditional robes and turbans stained their skin dark blue. In Japan, indigo became especially important during

1860-487: The Virgin Islands . However, France and Germany outlawed imported indigo in the 16th century to protect the local woad dye industry. In central Europe, indigo resist dyeing is a centuries-old skill that has received UNESCO Intangible Cultural Heritage of Humanity recognition. Newton used "indigo" to describe one of the two new primary colors he added to the five he had originally named, in his revised account of

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1920-564: The tBOC group , which suppresses intermolecular bonding. Heating of the tBOC indigo results in efficient thermal deprotection and regeneration of the parent H-bonded pigment. Treatment with sulfuric acid converts indigo into a blue-green derivative called indigo carmine (sulfonated indigo). It became available in the mid-18th century. It is used as a colorant for food, pharmaceuticals, and cosmetics. Indigo and some of its derivatives are known to be ambipolar organic semiconductors when deposited as thin films by vacuum evaporation. Indigo has

1980-435: The 1890s. The first " jeans " they invented were actually "waist-high overalls", consisting of denim pants with suspenders attached with buttons, but without a bib. From the beginning, denim overalls were popular workers' garments due to their durability. In fact, Levi Strauss & Co.'s slogan in the 1880s-1890s was "Never Rip, Never Tear". In 1911, Harry David Lee made the first bib overalls, made of pants with pockets with

2040-476: The 1960s onward. Overalls were especially popular among hip hop artists during the 1990s. In the 21st century, overalls have evolved into high-fashion garments. Designers such as Stella McCartney include them in ready-to-wear collections for men, women, and children. McCartney's children's overalls sell for as much as US$ 138 in the US. Levi Strauss & Co. and Lee were not the only companies making overalls in

2100-576: The 1970s, denim jeans were such an integral part of youth culture that automobile manufactures, beginning with American Motors Corporation began offering denim-like interior finishes. (Because denim cannot pass fire resistance safety standards, indigo-colored spun nylon or vinyl was used, with contrast-stitching and copper rivets helping to sell the effect.) A Levi's-branded trim package debuted with AMC's 1973 model year. Similar packages were available from Volkswagen from 1973 to 1975 (the "Jeans Beetle ") and from Jeep from 1975 through 1977. All denim

2160-519: The 19th century, English poet William Wordsworth referred to the plight of indigo dye workers of his hometown of Cockermouth in his autobiographical poem The Prelude . Speaking of their dire working conditions and the empathy that he felt for them, he wrote: Doubtless, I should have then made common cause With some who perished; haply perished too A poor mistaken and bewildered offering Unknown to those bare souls of miller blue A pre-industrial process for production of indigo white, used in Europe,

2220-525: The China blue method. Since 2004, freeze-dried indigo, or instant indigo, has become available. In this method, the indigo has already been reduced, and then freeze-dried into a crystal. The crystals are added to warm water to create the dye pot. As in a standard indigo dye pot, care has to be taken to avoid mixing in oxygen. Freeze-dried indigo is simple to use, and the crystals can be stored indefinitely as long as they are not exposed to moisture. Indigo dye

2280-520: The capacity of Davis's small shop, so he moved his production to the facilities of dry goods wholesaler Levi Strauss & Co. , which had been supplying Davis with bolts of denim fabric. Throughout the 20th century, denim was used for durable uniforms like those issued to staff of the French national railways. In the post-war years , the Royal Air Force issued olive-drab denim coveralls (colloquially known as "denims") for dirty work. By

2340-436: The color more easily tainted by other dye substances also present in these plants, typically leading to a greenish tinge. The precursor to indigo is indican , a colorless, water-soluble derivative of the amino acid tryptophan , and Indigofera leaves contain as much as 0.2–0.8% of this compound. Pressing cut leaves into a vat and soaking hydrolyzes the indican, releasing β- D - glucose and indoxyl . The indoxyl dimerizes in

2400-409: The conjugation of the double bonds , i.e. the double bonds within the molecule are adjacent and the molecule is planar. In indigo white, the conjugation is interrupted because the molecule is non-planar. The benzene rings in indigo can be modified to give a variety of related dyestuffs. Thioindigo , where the two NH groups are replaced by S atoms, is deep red. Tyrian purple is a dull purple dye that

2460-404: The cotton, the woven form of which (typically called 'stretch denim') may have a elasticity of up to 15%. Denim was originally dyed with indigo dye extracted from plants, often from the genus Indigofera . In South Asia, indigo dye was extracted from the dried and fermented leaves of Indigofera tinctoria ; this is the plant that is now known as "true indigo" or "natural indigo". In Europe,

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2520-420: The easy to obtain aniline provided a new and economically attractive route. BASF developed a commercially feasible manufacturing process that was in use by 1897, at which time 19,000 tons of indigo were being produced from plant sources. This had dropped to 1,000 tons by 1914 and continued to contract. By 2011, 50,000 tons of synthetic indigo were being produced worldwide. Indigo is a challenging dye because it

2580-520: The garment industry. In the 1930s, the poorest segments of the American population wore overalls: farmers , miners , loggers , and railroad workers. They were most commonly worn by men and boys in the Southern and Midwestern United States . They can be seen in many of Walker Evans 's photographs. Bib overalls (in different colors and textiles) became popular garments among American youth from

2640-468: The insoluble form of indigo onto the fabric. The indigo was then reduced in a sequence of baths of iron(II) sulfate , with air oxidation between each immersion. The China blue process could make sharp designs, but it could not produce the dark hues possible with the pencil blue method. Around 1880, the 'glucose process' was developed. It finally enabled the direct printing of indigo onto fabric and could produce inexpensive dark indigo prints unattainable with

2700-452: The instep, worn as part of the mess dress and full dress uniforms of cavalry regiments. Denim Denim is a sturdy cotton warp-faced textile in which the weft passes under two or more warp threads. This twill weave produces a diagonal ribbing that distinguishes it from cotton duck . Denim, as it is recognized today, was first produced in Nîmes , France. Denim

2760-462: The late 19th and 20th centuries. Shortalls (a contraction of the words "short" and "overalls") are with the lower part adapted into shorts . Salopettes is the French word for bib-and-brace overalls. The word is used in English for a similar garment to overalls worn for sailing , skiing , diving , and other heavy-duty activities. They are made of wind-and-waterproof trousers, traditionally with

2820-574: The lengthy and dangerous land routes which had previously been used. Consequently, the importation and use of indigo in Europe rose significantly. Much European indigo from Asia arrived through ports in Portugal, the Netherlands, and England. Many indigo plantations were established by European powers in tropical climates. Spain imported the dye from its colonies in Central and South America, and it

2880-538: The mixture, and after 12–15 hours of fermentation yields the yellow, water-soluble leucoindigo . Subsequent exposure to air forms the blue, water-insoluble indigo dye. The dye precipitates from the fermented leaf solution upon oxidation, but may also be precipitated when mixed with a strong base such as lye . The solids are filtered, pressed into cakes, dried, and powdered. The powder is then mixed with various other substances to produce different shades of blue and purple. Natural sources of indigo also include mollusks:

2940-622: The rainbow in Lectiones Opticae of 1675. Because of its high value as a trading commodity, indigo was often referred to as blue gold. Throughout West Africa, Indigo was the foundation of centuries-old textile traditions. From the Tuareg nomads of the Sahara to Cameroon , clothes dyed with indigo signified wealth. Women dyed the cloth in most areas, with the Yoruba of Nigeria and

3000-484: The selvedge requires greater care of assemblage. The thickness of denim can vary greatly, with a yard of fabric weighing anywhere from 9 to 32 oz (260 to 910 g), with 11 to 14 oz (310 to 400 g) being typical. Denim is frequently used for a wide array of consumer products, including: Denim has been a medium for many artists. At least one artist, Ian Berry , uses old or recycled denim, exclusively in crafting his portraits and other scenes. In 2020,

3060-463: The south, Persicaria tinctoria (dyer's knotweed) was the most important blue dyestuff in East Asia; however, the crop produced less dyestuff than the average crop of indigo, and was quickly surpassed in favour of the more economical Indigofera tinctoria plant. In Central and South America, the species grown is Indigofera suffruticosa , also known as anil , and in India, an important species

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3120-411: The use of Isatis tinctoria , or woad, can be traced back to the 8th century BC, although it was eventually replaced by Indigofera tinctoria as the superior dye product. However, most denim today is dyed with synthetic indigo dye. In all cases, the yarn undergoes a repeated sequence of dipping and oxidation—the more dips, the stronger the color of the indigo. Before 1915, cotton yarns were dyed using

3180-486: The worldwide denim market equaled US$ 57.3 billion, with demand growing by 5.8% and supply growing by 8% annually. Over 50% of denim is produced in Asia, most of it in China , India , Turkey , Pakistan , and Bangladesh . Globally, the denim industry is expected to grow at a CAGR of over 4.8% from 2022 to 2026, with the market value expected to increase from $ 57.3 billion to $ 76.1 billion. Indigo dye Indigo dye

3240-450: Was Indigofera arrecta , Natal indigo. In Europe, Isatis tinctoria , commonly known as woad, was used for dyeing fabrics blue, containing the same dyeing compounds as indigo, also referred to as indigo. Several plants contain indigo, which, when exposed to an oxidizing source such as atmospheric oxygen, reacts to produce indigo dye; however, the relatively low concentrations of indigo in these plants make them difficult to work with, with

3300-729: Was a luxury item imported to the Mediterranean from India by Arab merchants. India was a primary supplier of indigo to Europe as early as the Greco-Roman era. The association of India with indigo is reflected in the Greek word for the dye, indikón ( Ἰνδικόν , Indian). The Romans latinized the term to indicum , which passed into Italian dialect and eventually into English as the word indigo. In Bengal indigo cultivators revolted against exploitative working conditions created by European merchants and planters in what became known as

3360-515: Was a major crop in Haiti and Jamaica, with much or all of the labor performed by enslaved Africans and African Americans. In the Spanish colonial era, intensive production of indigo for the world market in the region of modern El Salvador entailed such unhealthy conditions that the local indigenous population, forced to labor in pestilential conditions, was decimated. Indigo plantations also thrived in

3420-534: Was highly useful for obtaining indigo and many of its derivatives on the laboratory scale, but proved impractical for industrial-scale synthesis. Johannes Pfleger and Karl Heumann  [ de ] eventually came up with industrial mass production synthesis from aniline by using mercury as a catalyst. The method was discovered by an accident by Karl Heumann in Zurich which involved a broken thermometer. The first commercially practical route of producing indigo

3480-428: Was most often applied by pencil or brush, could be used to achieve dark hues. Arsenic trisulfide and a thickener were added to the indigo vat. The arsenic compound delayed the oxidation of the indigo long enough to paint the dye onto fabrics. The second method was known as 'China blue' due to its resemblance to Chinese blue-and-white porcelain. Instead of using an indigo solution directly, the process involved printing

3540-507: Was obtained from those in the genus Indigofera , which are native to the tropics, notably the Indian Subcontinent. The primary commercial indigo species in Asia was true indigo ( Indigofera tinctoria , also known as I. sumatrana ). A common alternative used in the relatively colder subtropical locations such as Japan's Ryukyu Islands and Taiwan is Strobilanthes cusia . Until the introduction of Indigofera species from

3600-476: Was to dissolve the indigo in stale urine, which contains ammonia. A more convenient reductive agent is zinc. Another pre-industrial method, used in Japan, was to dissolve the indigo in a heated vat in which a culture of thermophilic , anaerobic bacteria was maintained. Some species of such bacteria generate hydrogen as a metabolic product, which convert insoluble indigo into soluble indigo white. Cloth dyed in such

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