Soap

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Handmade soap cropped and simplified.jpg
Two equivalent images of the chemical structure of sodium stearate, a typical ingredient found in bar soaps. NaStearate.png
Two equivalent images of the chemical structure of sodium stearate, a typical ingredient found in bar soaps.
The chemical structure of sodium laureth sulfate, a typical ingredient found in liquid soaps. Sodium laureth sulfate structure.png
The chemical structure of sodium laureth sulfate, a typical ingredient found in liquid soaps.
Greases for automotive applications contain soaps. Wheel Bearing Grease.jpg
Greases for automotive applications contain soaps.

Soap is a salt of a fatty acid [1] used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are used as thickeners, components of some lubricants, and precursors to catalysts.

Contents

When used for cleaning, soap solubilizes particles and grime, which can then be separated from the article being cleaned. In hand washing, as a surfactant, when lathered with a little water, soap kills microorganisms by disorganizing their membrane lipid bilayer and denaturing their proteins. It also emulsifies oils, enabling them to be carried away by running water. [2]

Soap is created by mixing fats and oils with a base, [3] as opposed to detergent which is created by combining chemical compounds in a mixer.

Humans have used soap for millennia. Evidence exists of the production of soap-like materials in around 2800 BC in ancient Babylon.

Types of soaps

A collection of decorative bar soaps, as often found in hotels Decorative Soaps.jpg
A collection of decorative bar soaps, as often found in hotels

Since they are salts of fatty acids, soaps have the general formula (RCO2)nMn+ (Where R is an alkyl, M is a metal and n is the charge of the cation). The major classification of soaps is determined by the identity of Mn+. When M is Na or K, the soaps are called toilet soaps, used for handwashing. Many metal dications (Mg2+, Ca2+, and others) give metallic soap. When M is Li, the result is lithium soap (e.g., lithium stearate), which is used in high-performance greases. [4]

Non-toilet soaps

Soaps are key components of most lubricating greases and thickeners. Greases are usually emulsions of calcium soap or lithium soap and mineral oil. [5] Many other metallic soaps are also useful, including those of aluminium, sodium, and mixtures thereof. Such soaps are also used as thickeners to increase the viscosity of oils. In ancient times, lubricating greases were made by the addition of lime to olive oil. [6]

Metal soaps are also included in modern artists' oil paints formulations as a rheology modifier. [7]

Production of metallic soaps

Most metal soaps are prepared by neutralization of purified fatty acids:

2 RCO2H + CaO → (RCO2)2Ca + H2O

Toilet soaps

In a domestic setting, "soap" usually refers to what is technically called a toilet soap, used for household and personal cleaning. When used for cleaning, soap solubilizes particles and grime, which can then be separated from the article being cleaned. The insoluble oil/fat molecules become associated inside micelles, tiny spheres formed from soap molecules with polar hydrophilic (water-attracting) groups on the outside and encasing a lipophilic (fat-attracting) pocket, which shields the oil/fat molecules from the water making it soluble. Anything that is soluble will be washed away with the water.

Structure of a micelle, a cell-like structure formed by the aggregation of soap subunits (such as sodium stearate): The exterior of the micelle is hydrophilic (attracted to water) and the interior is lipophilic (attracted to oils). MicelleColor.png
Structure of a micelle, a cell-like structure formed by the aggregation of soap subunits (such as sodium stearate): The exterior of the micelle is hydrophilic (attracted to water) and the interior is lipophilic (attracted to oils).

Production of toilet soaps

The production of toilet soaps usually entails saponification of triglycerides, which are vegetable or animal oils and fats. An alkaline solution (often lye or sodium hydroxide) induces saponification whereby the triglyceride fats first hydrolyze into salts of fatty acids. Glycerol (glycerin) is liberated. The glycerin can remain in the soap product as a softening agent, although it is sometimes separated. [8]

The type of alkali metal used determines the kind of soap product. Sodium soaps, prepared from sodium hydroxide, are firm, whereas potassium soaps, derived from potassium hydroxide, are softer or often liquid. Historically, potassium hydroxide was extracted from the ashes of bracken or other plants. Lithium soaps also tend to be hard. These are used exclusively in greases.

For making toilet soaps, triglycerides (oils and fats) are derived from coconut, olive, or palm oils, as well as tallow. [9] Triglyceride is the chemical name for the triesters of fatty acids and glycerin. Tallow, i.e., rendered beef fat, is the most available triglyceride from animals. Each species offers quite different fatty acid content, resulting in soaps of distinct feel. The seed oils give softer but milder soaps. Soap made from pure olive oil, sometimes called Castile soap or Marseille soap, is reputed for its particular mildness. The term "Castile" is also sometimes applied to soaps from a mixture of oils, but a high percentage of olive oil.

Fatty acid content of various fats used for soapmaking
Lauric acid Myristic acid Palmitic acid Stearic acid Oleic acid Linoleic acid Linolenic acid
fatsC12 saturatedC14 saturatedC16 saturatedC18 saturatedC18 monounsaturatedC18 diunsaturatedC18 triunsaturated
Tallow 0428233521
Coconut oil 481893720
Palm kernel oil 4616831220
Palm oil 014443790
Laurel oil 5400015170
Olive oil 0011278100
Canola oil 013258923

History

Ancient Middle East

Box for Amigo del Obrero (Worker's Friend) soap from the 20th century, part of the Museo del Objeto del Objeto collection MODOAmigo.jpg
Box for Amigo del Obrero (Worker's Friend) soap from the 20th century, part of the Museo del Objeto del Objeto collection

The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BC in ancient Babylon. [10] A formula for soap consisting of water, alkali, and cassia oil was written on a Babylonian clay tablet around 2200 BC. [11]

The Ebers papyrus (Egypt, 1550 BC) indicates the ancient Egyptians bathed regularly and combined animal and vegetable oils with alkaline salts to create a soap-like substance. Egyptian documents mention a similar substance was used in the preparation of wool for weaving. [12]

In the reign of Nabonidus (556–539 BC), a recipe for soap consisted of uhulu [ashes], cypress [oil] and sesame [seed oil] "for washing the stones for the servant girls". [13]

In ancient Israel, the ashes from barilla plants, such as species of Salsola, saltwort ( Seidlitzia rosmarinus ) and Anabasis , were used in soap production, known as potash. [14] [15] Soap made from potash (a concentrate of burnt wood or vegetable ashes mixed with lard or olive oil) is alkaline. If animal lard were used, it was heated and kept lukewarm (not boiling hot; neither cold). Lard, collected from suet, needed to be rendered and strained before being used with ashes (with the recommended consistency of 1 cup of lard to 3/8 cup of concentrated ash water). Traditionally, olive oil was used instead of animal lard throughout the Levant, which was boiled in a copper cauldron for several days. [16] As the boiling progresses, alkali ashes and smaller quantities of quicklime were added, and constantly stirred. [16] In the case of lard, it required constant stirring while kept lukewarm until it began to trace. Once it began to thicken, the brew was poured into a mold and left to cool and harden for 2 weeks. After hardening, it was cut into smaller cakes. Aromatic herbs were often added to the rendered soap to impart their fragrance, such as yarrow leaves, lavender, germander, etc. The ancient method here described is still in use in the production of Nabulsi soap.

Roman Empire

The word sapo, Latin for soap, likely was borrowed from an early Germanic language and is cognate with Latin sebum, "tallow". It first appears in Pliny the Elder's account, [17] Historia Naturalis , which discusses the manufacture of soap from tallow and ashes, but the only use he mentions for it is as a pomade for hair; he mentions rather disapprovingly that the men of the Gauls and Germans were more likely to use it than their female counterparts. [18] The Romans avoided washing with harsh soaps before encountering the milder soaps used by the Gauls around 58 BC. [19] Aretaeus of Cappadocia, writing in the 2nd century AD, observes among "Celts, which are men called Gauls, those alkaline substances that are made into balls [...] called soap". [20] The Romans' preferred method of cleaning the body was to massage oil into the skin and then scrape away both the oil and any dirt with a strigil. The Gauls used soap made from animal fat.

Zosimos of Panopolis, circa 300 AD, describes soap and soapmaking. [21] Galen describes soap-making using lye and prescribes washing to carry away impurities from the body and clothes. The use of soap for personal cleanliness became increasingly common in the 2nd century AD. According to Galen, the best soaps were Germanic, and soaps from Gaul were second best. [21]

Ancient China

A detergent similar to soap was manufactured in ancient China from the seeds of Gleditsia sinensis. [22] Another traditional detergent is a mixture of pig pancreas and plant ash called zhuyizi (simplified Chinese :猪胰子; traditional Chinese :豬胰子; pinyin :zhūyízǐ). True soap, made of animal fat, did not appear in China until the modern era. [23] Soap-like detergents were not as popular as ointments and creams. [22]

Islamic Middle East

Hard toilet soap with a pleasant smell was produced in the Middle East during the Islamic Golden Age, when soap-making became an established industry. Recipes for soap-making are described by Muhammad ibn Zakariya al-Razi (854–925), who also gave a recipe for producing glycerine from olive oil. In the Middle East, soap was produced from the interaction of fatty oils and fats with alkali. In Syria, soap was produced using olive oil together with alkali and lime. Soap was exported from Syria to other parts of the Muslim world and to Europe. [24]

A 12th-century Islamic document describes the process of soap production. [25] It mentions the key ingredient, alkali, which later becomes crucial to modern chemistry, derived from al-qaly or "ashes".

By the 13th century, the manufacture of soap in the Islamic world had become virtually industrialized, with sources in Nablus, Fes, Damascus, and Aleppo. [26] [27]

Medieval Europe

Soapmakers in Naples were members of a guild in the late sixth century (then under the control of the Eastern Roman Empire), [28] and in the eighth century, soap-making was well known in Italy and Spain. [29] The Carolingian capitulary De Villis, dating to around 800, representing the royal will of Charlemagne, mentions soap as being one of the products the stewards of royal estates are to tally. The lands of Medieval Spain were a leading soapmaker by 800, and soapmaking began in the Kingdom of England about 1200. [30] Soapmaking is mentioned both as "women's work" and as the produce of "good workmen" alongside other necessities, such as the produce of carpenters, blacksmiths, and bakers. [31]

In Europe, soap in the 9th century was produced from animal fats and had an unpleasant smell. Hard toilet soap with a pleasant smell was later imported from the Middle East. [24]

15th–18th centuries

Advertising at Dobbins' medicated toilet soap Dobbins' medicated toilet soap, advertising, 1869.jpg
Advertising at Dobbins' medicated toilet soap
A 1922 magazine advertisement for Palmolive Soap Palmolive soap 1922 advertisement ladies home journal.jpeg
A 1922 magazine advertisement for Palmolive Soap
Liquid soap Liquid antibacterial soap.jpg
Liquid soap
Manufacturing process of soaps/detergents Soap and Detergent manufacturing process 03.png
Manufacturing process of soaps/detergents

In France, by the second half of the 15th century, the semi-industrialized professional manufacture of soap was concentrated in a few centers of ProvenceToulon, Hyères, and Marseille—which supplied the rest of France. [32] In Marseilles, by 1525, production was concentrated in at least two factories, and soap production at Marseille tended to eclipse the other Provençal centers. [33] English manufacture tended to concentrate in London. [34]

Finer soaps were later produced in Europe from the 16th century, using vegetable oils (such as olive oil) as opposed to animal fats. Many of these soaps are still produced, both industrially and by small-scale artisans. Castile soap is a popular example of the vegetable-only soaps derived from the oldest "white soap" of Italy. In 1634 Charles I granted the newly formed Society of Soapmakers a monopoly in soap production who produced certificates from ‘foure Countesses, and five Viscountesses, and divers other Ladies and Gentlewomen of great credite and quality, besides common Laundresses and others’, testifying that ‘the New White Soap washeth whiter and sweeter than the Old Soap’. [35]

Industrially manufactured bar soaps became available in the late 18th century, as advertising campaigns in Europe and America promoted popular awareness of the relationship between cleanliness and health. [36] In modern times, the use of soap has become commonplace in industrialized nations due to a better understanding of the role of hygiene in reducing the population size of pathogenic microorganisms. [37]

19th century

Ad for Soapine, circa 1900, indicating that it is made of whale oil Kendall Mfg. Co. (estab. 1827) (3093594402).jpg
Ad for Soapine, circa 1900, indicating that it is made of whale oil

Until the Industrial Revolution, soapmaking was conducted on a small scale and the product was rough. In 1780, James Keir established a chemical works at Tipton, for the manufacture of alkali from the sulfates of potash and soda, to which he afterwards added a soap manufactory. The method of extraction proceeded on a discovery of Keir's. In 1790, Nicolas Leblanc discovered how to make alkali from common salt. [19] Andrew Pears started making a high-quality, transparent soap in 1807 [38] in London. His son-in-law, Thomas J. Barratt, opened a factory in Isleworth in 1862.

During the Restoration era (February 1665 – August 1714) a soap tax was introduced in England, which meant that until the mid-1800s, soap was a luxury, used regularly only by the well-to-do. The soap manufacturing process was closely supervised by revenue officials who made sure that soapmakers' equipment was kept under lock and key when not being supervised. Moreover, soap could not be produced by small makers because of a law which stipulated that soap boilers must manufacture a minimum quantity of one imperial ton at each boiling, which placed the process beyond reach of the average person. The soap trade was boosted and deregulated when the tax was repealed in 1853. [39] [40] [41]

William Gossage produced low-priced, good-quality soap from the 1850s. Robert Spear Hudson began manufacturing a soap powder in 1837, initially by grinding the soap with a mortar and pestle. American manufacturer Benjamin T. Babbitt introduced marketing innovations that included sale of bar soap and distribution of product samples. William Hesketh Lever and his brother, James, bought a small soap works in Warrington in 1886 and founded what is still one of the largest soap businesses, formerly called Lever Brothers and now called Unilever. These soap businesses were among the first to employ large-scale advertising campaigns.

Liquid soap

Liquid soap was not invented until the nineteenth century; in 1865, William Shepphard patented a liquid version of soap. [42] In 1898, B.J. Johnson developed a soap derived from palm and olive oils; his company, the B.J. Johnson Soap Company, introduced "Palmolive" brand soap that same year. [43] This new brand of soap became popular rapidly, and to such a degree that B.J. Johnson Soap Company changed its name to Palmolive. [44]

In the early 1900s, other companies began to develop their own liquid soaps. Such products as Pine-Sol and Tide appeared on the market, making the process of cleaning things other than skin, such as clothing, floors, and bathrooms, much easier.

Liquid soap also works better for more traditional or non-machine washing methods, such as using a washboard. [45]

Soap-making for hobbyists

A variety of methods are available for hobbyists to make soap. [46] Most soapmakers use processes where the glycerol remains in the product, and the saponification continues for many days after the soap is poured into molds. The glycerol is left during the hot-process method, but at the high temperature employed, the reaction is practically completed in the kettle, before the soap is poured into molds. This simple and quick process is employed in small factories all over the world.

Handmade soap from the cold process also differs from industrially made soap in that an excess of fat is used, beyond that needed to consume the alkali (in a cold-pour process, this excess fat is called "superfatting"), and the glycerol left in acts as a moisturizing agent. However, the glycerine also makes the soap softer. Addition of glycerol and processing of this soap produces glycerin soap. Superfatted soap is more skin-friendly than one without extra fat, although it can leave a "greasy" feel. Sometimes, an emollient is added, such as jojoba oil or shea butter. [47] Sand or pumice may be added to produce a scouring soap. The scouring agents serve to remove dead cells from the skin surface being cleaned. This process is called exfoliation.

The lye is dissolved in water. Pouring lye into water to make soap.jpg
The lye is dissolved in water.

To make antibacterial soap, compounds such as triclosan or triclocarban can be added. There is some concern that use of antibacterial soaps and other products might encourage antibiotic resistance in microorganisms. [48]

See also

Personal use soap

Related Research Articles

Triglyceride

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

Glycerol Chemical compound

Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in those lipids known as glycerides. Due to having antimicrobial and antiviral properties it is widely used in FDA approved wound and burn treatments. It can also be used as an effective marker to measure liver disease. It is also widely used as a sweetener in the food industry and as a humectant in pharmaceutical formulations. Owing to the presence of three hydroxyl groups, glycerol is miscible with water and is hygroscopic in nature.

Vegetable oil

Vegetable oils, or vegetable fats, are oils extracted from seeds, or less often, from other parts of fruits. Like animal fats, vegetable fats are mixtures of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of fats from seeds. Olive oil, palm oil, and rice bran oil are examples of fats from other parts of fruits. In common usage, vegetable oil may refer exclusively to vegetable fats which are liquid at room temperature. Vegetable oils are usually edible; non-edible oils derived mainly from petroleum are termed mineral oils.

Tallow rendered form of beef or mutton fat

Tallow is a rendered form of beef or mutton fat, and is primarily made up of triglycerides. It is solid at room temperature. Unlike suet, tallow can be stored for extended periods without the need for refrigeration to prevent decomposition, provided it is kept in an airtight container to prevent oxidation.

Saponification is a process that involves the conversion of fat, oil, or lipid, into soap and alcohol by the action of heat in the presence of aqueous alkali. Soaps are salts of fatty acids and fatty acids are mono that have long carbon chains e.g. sodium palmitate.

Stearin

Stearin, or tristearin, or glyceryl tristearate is an odourless, white powder. It is a triglyceride derived from three units of stearic acid. Most triglycerides are derived from at least two and more commonly three different fatty acids. Like other triglycerides, stearin can crystallise in three polymorphs. For stearin, these melt at 54 (α-form), 65, and 72.5 °C (β-form).

Cottonseed oil

Cottonseed oil is cooking oil from the seeds of cotton plants of various species, mainly Gossypium hirsutum and Gossypium herbaceum, that are grown for cotton fiber, animal feed, and oil.

Oleic acid Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates.

Biodiesel production is the process of producing the biofuel, biodiesel, through the chemical reactions of transesterification and esterification. This involves vegetable or animal fats and oils being reacted with short-chain alcohols. The alcohols used should be of low molecular weight. Ethanol is the most used because of its low cost, however, greater conversions into biodiesel can be reached using methanol. Although the transesterification reaction can be catalyzed by either acids or bases, the base-catalyzed reaction is more common. This path has lower reaction times and catalyst cost than those acid catalysis. However, alkaline catalysis has the disadvantage of high sensitivity to both water and free fatty acids present in the oils.

Saponification value

Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample as triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice-versa. Practically, fats or oils with high saponification value are more suitable for soap making.

Crisco American brand of shortening

Crisco is a brand of shortening produced by The J.M. Smucker Company popular in the United States. Introduced in June 1911 by Procter & Gamble, it was the first shortening to be made entirely of vegetable oil (cottonseed). Additional products marketed by Smucker under the Crisco brand include a cooking spray, various olive oils, and other cooking oils, including canola, corn, peanut, olive, sunflower, and blended oils.

Glycerin soap

Glycerin soaps are soaps that contain glycerin, a component of fat or oil. They are recognizably different from other soaps because they are translucent. The clarity is due to the alignment of the soap molecules, which can be induced through the addition of alcohol and sugar. This is usually done for homemade glycerin soaps that are not remeltable.

Monoglyceride

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

Marseille soap

Marseille soap or Savon de Marseille is a traditional hard soap made from vegetable oils that has been produced around Marseille, France, for about 600 years. The first documented soapmaker was recorded there in about 1370. By 1688, Louis XIV introduced regulations in the Edict of Colbert limiting the use of the name savon de Marseille to olive oil based soaps. The law has since been amended to allow other vegetable oils to be used.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum “olive oil”). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

Lard

Lard is a semi-solid white fat product obtained by rendering the fatty tissue of the pig. It is distinguished from tallow, a similar product derived from fat of cattle or sheep.

In the food industry and biochemistry, interesterification (IE) is a process that rearranges the fatty acids of a fat product, typically a mixture of triglyceride. The process implies breaking and reforming the ester bonds C–O–C that connect the fatty acid chains to the glycerol hubs of the fat molecules. These reactions are performed by inorganic catalysts, yielding what is called chemical interesterification (CIE) in the industry; or by enzymes, in the so-called enzymatic interesterification (EIE).

Diglyceride Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

Saltwater soap, also called sailors' soap, is a potassium-based soap for use with seawater. Inexpensive common commercial soap will not lather or dissolve in seawater due to high levels of sodium chloride in the water. Similarly, common soap does not work as well as potassium-based soap in hard water where calcium replaces the sodium, making residual insoluble "scum" due to the insolubility of the soap residue. To be an effective cleaning agent, soap must be able to dissolve in water.

Cooking oil

Cooking oil is plant, animal, or synthetic fat used in frying, baking, and other types of cooking. It is also used in food preparation and flavouring not involving heat, such as salad dressings and bread dippings like bread dips, and may be called edible oil.

References

  1. IUPAC , Compendium of Chemical Terminology , 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006) " soap ". doi : 10.1351/goldbook.S05721
  2. S., Tumosa, Charles (2001-09-01). "A Brief History of Aluminum Stearate as a Component of Paint". cool.conservation-us.org. Archived from the original on 2017-03-18. Retrieved 2017-04-05.
  3. "What's The Difference Between Soap and Detergent | cleancult".
  4. Klaus Schumann; Kurt Siekmann (2005). "Soaps". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_247. ISBN   978-3527306732.
  5. see the main Grease (lubricant) article
  6. Thorsten Bartels; et al. (2005). "Lubricants and Lubrication". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_423. ISBN   978-3527306732.
  7. S., Tumosa, Charles (2001-09-01). "A Brief History of Aluminum Stearate as a Component of Paint". cool.conservation-us.org. Archived from the original on 2017-03-18. Retrieved 2017-03-17.
  8. Cavitch, Susan Miller. The Natural Soap Book. Storey Publishing, 1994 ISBN   0-88266-888-9.
  9. David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a10_245.pub2
  10. Willcox, Michael (2000). "Soap". In Hilda Butler (ed.). Poucher's Perfumes, Cosmetics and Soaps (10th ed.). Dordrecht: Kluwer Academic Publishers. p. 453. ISBN   978-0-7514-0479-1. Archived from the original on 2016-08-20. The earliest recorded evidence of the production of soap-like materials dates back to around 2800 BCE in ancient Babylon.
  11. Adventist Youth Honors Answer Book/Arts and Crafts/Soap Craft (General Conference). Wikibooks. Retrieved 8 March 2020.
  12. Adventist Youth Honors Answer Book/Arts and Crafts/Soap Craft (General Conference). Wikibooks. Retrieved 8 March 2020.
  13. Noted in Levey, Martin (1958). "Gypsum, salt and soda in ancient Mesopotamian chemical technology". Isis. 49 (3): 336–342 (341). doi:10.1086/348678. JSTOR   226942.
  14. Zohar Amar, Flora of the Bible, Jerusalem 2012, s.v. ברית, p. 216 (note 34) OCLC   783455868.
  15. Abu-Rabiʻa, ʻAref (2001). Bedouin Century: Education and Development among the Negev Tribes in the Twentieth Century. New York. pp. 47–48. OCLC   47119256.
  16. 1 2 Cohen, Amnon (1989). Economic Life in Ottoman Jerusalem. Cambridge: Cambridge University Press. p. 81. ISBN   0521365511.
  17. soaps p Archived 2011-02-08 at the Wayback Machine . Etymonline.com. Retrieved on 2011-11-20.
  18. Pliny the Elder, Natural History , XXVIII.191. See also Martial, Epigrammata, VIII, 33, 20. Archived 2013-01-21 at the Wayback Machine
  19. 1 2 Foreman, Amanda (October 4, 2019). "The Long Road to Cleanliness". www.wsj.com. Retrieved October 6, 2019.
  20. Aretaeus, The Extant Works of Aretaeus, the Cappadocian, ed. and tr. Francis Adams (London) 1856:238 and 496 Archived 2016-06-09 at the Wayback Machine , noted in Michael W. Dols, "Leprosy in medieval Arabic medicine" Journal of the History of Medicine 1979:316 note 9; the Gauls with whom the Cappadocian would have been familiar are those of Anatolian Galatia.
  21. 1 2 Partington, James Riddick; Hall, Bert S (1999). A History of Greek Fire and Gun Powder . JHU Press. p.  307. ISBN   978-0-8018-5954-0.
  22. 1 2 Jones, Geoffrey (2010). "Cleanliness and Civilization". Beauty Imagined: A History of the Global Beauty Industry. Oxford University Press. ISBN   978-0-19-160961-9. Archived from the original on 2016-05-07.
  23. Benn, Charles (2002). Everyday Life in the Tang Dynasty. Oxford University Press. p. 116. ISBN   978-0-19-517665-0. Archived from the original on 2016-05-05.
  24. 1 2 Ahmad Y. al-Hassan (2001), Science and Technology in Islam: Technology and applied sciences, pages 73-74 Archived 2017-12-09 at the Wayback Machine , UNESCO
  25. BBC Science and Islam Part 2, Jim Al-Khalili. BBC Productions. Accessed 30 January 2012.
  26. Phillips, Michael (March 11, 2008). "Nablus' olive oil soap: a Palestinian tradition lives on". Institute for Middle East Understanding (IMEU). Archived from the original on July 20, 2008. Retrieved 2008-03-27.
  27. "Craft Traditions of Palestine". Sunbula. Archived from the original on March 21, 2008. Retrieved 2008-04-18.
  28. footnote 48, p. 104, Understanding the Middle Ages: the transformation of ideas and attitudes in the Medieval world, Harald Kleinschmidt, illustrated, revised, reprint edition, Boydell & Brewer, 2000, ISBN   0-85115-770-X.
  29. Anionic and Related Lime Soap Dispersants, Raymond G. Bistline Jr., in Anionic Surfactants: Organic Chemistry, Helmut Stache, ed., Volume 56 of Surfactant science series, CRC Press, 1996, chapter 11, p. 632, ISBN   0-8247-9394-3.
  30. www.soap-flakes.com Archived 2015-05-26 at the Wayback Machine . soap-flakes.com. Retrieved on 2015-10-31.
  31. Robinson, James Harvey (1904). Readings in European History: Vol. I. Ginn and co. Archived from the original on 2009-09-25.
  32. Nef, John U. (1936). "A Comparison of Industrial Growth in France and England from 1540 to 1640: III". The Journal of Political Economy. 44 (5): 643–666 (660ff.). doi:10.1086/254976. JSTOR   1824135.
  33. Barthélemy, L. (1883) "La savonnerie marseillaise", noted by Nef 1936:660 note 99.
  34. Nef 1936:653, 660.
  35. Keith Thomas, 'Noisomeness,' London Review of Books, Vol. 42 No. 14, 16 July 2020
  36. McNeil, Ian (1990). An Encyclopaedia of the History of Technology. Taylor & Francis. pp. 2003–205. ISBN   978-0-415-01306-2. Archived from the original on 2016-05-05.
  37. Ahveninen, Anna (2020-03-31). "Hand sanitiser or soap: making an informed choice for COVID-19". Curious. Retrieved 2020-08-04.
  38. Pears, Francis (1859). The Skin, Baths, Bathing, and Soap. The author. pp. 100–. Archived from the original on 2016-05-04.
  39. "The Soap Tax". The Spectator Archive. The Spectator, London. Archived from the original on 24 March 2017. Retrieved 23 March 2017.
  40. "Repeal of the Soap Tax". Hansard. UK Parliament. Archived from the original on 24 March 2017. Retrieved 23 March 2013.
  41. Hansard, Thomas Curson (1864). Hansard's Parliamentary Debates. Uxbridge, England: Forgotten Books. pp. 363–374. ISBN   9780243121328.
  42. ,"Improved liquid soap",issued 1865-08-22
  43. Prigge, Matthew (2018-01-25). "The Story Behind This Bar of Palmolive Soap". Milwaukee Magazine. Retrieved 2019-06-27.
  44. "Colgate-Palmolive Company History: Creating Bright Smiles for 200 Years". Colgate-Palmolive Company. Retrieved 17 October 2012.
  45. "The History of Liquid Soap". Blue Aspen Originals. Archived from the original on 1 December 2012. Retrieved 17 October 2012.
  46. Garzena, Patrizia, and Tadiello, Marina (2013). The Natural Soapmaking Handbook. Online information and Table of Contents Archived 2015-07-30 at the Wayback Machine . ISBN   978-0-9874995-0-9/
  47. "The Process of Making Soap". edtech.mcc.edu. Retrieved 8 March 2020.
  48. "Antibacterial Soaps Concern Experts". ABC News. 2006-01-06. Archived from the original on 12 November 2014. Retrieved 12 November 2014.

Further reading