Editing Detergent

{{Short description|Surfactants with cleansing properties}}
{{Use dmy dates|date=November 2018}}
{{other uses}}
[[File:Diskflaskor.JPG|thumb|Detergents]]
A '''detergent''' is a [[surfactant]] or a [[mixture]] of surfactants with [[Cleanliness|cleansing]] properties when in [[Concentration|dilute]] [[Solution (chemistry)|solutions]].<ref name=":0">{{GoldBookRef |title=detergent |file=D01643  |accessdate=2013-01-12}}</ref> There are a large variety of detergents.  A common family is the [[alkylbenzene sulfonates]], which are [[soap]]-like compounds that are more soluble than soap in [[hard water]], because the polar [[sulfonate]] is less likely than the polar [[carboxylate]] of soap to bind to calcium and other ions found in hard water.

==Definitions==
{{wiktionary|detergent}}

The word ''detergent'' is derived from the Latin adjective ''detergens'', from the verb ''detergere'', meaning to wipe or polish off. Detergent can be defined as a [[surfactant]] or a [[mixture]] of surfactants with cleansing properties when in [[Concentration|dilute]] [[Solution (chemistry)|solutions]].<ref name=":0"/> However, conventionally, detergent is used to mean synthetic cleaning compounds as opposed to ''[[soap]]'' (a salt of the natural [[fatty acid]]), even though soap is also a detergent in the true sense.<ref>{{cite book|author=NIIR Board of Consultants Engineers |title=The Complete Technology Book on Detergents |edition=2nd Revised|url={{Google Books |qgC_CwAAQBAJ|page=1|plain-url=yes}}|date=2013|isbn=9789381039199|page=1 |publisher=Niir Project Consultancy Services |via=Google Books}}</ref> In domestic contexts, the term ''detergent'' refers to household cleaning products such as ''[[laundry detergent]]'' or ''[[Dishwashing liquid|dish detergent]]'', which are in fact complex mixtures of different compounds, not all of which are by themselves detergents.

Detergency is the ability to remove unwanted substances termed 'soils' from a substrate (e.g., clothing).<ref>{{cite book|editor=Arno Cahn |title=5th World Conference on Detergents|url={{Google Books |VMqSJROG_WYC|page=154|plain-url=yes}}|date=2003|isbn=9781893997400|page=154 |publisher=The American Oil Chemists Society |via=Google Books}}</ref>

==Structure and properties==
Detergents are a group of compounds with an [[amphiphilic]] structure, where each molecule has a [[hydrophilic]] (polar) head and a long [[hydrophobic]] (non-polar) tail. The hydrophobic portion of these molecules may be straight- or branched-chain [[hydrocarbon]]s, or it may have a [[steroid]] structure. The hydrophilic portion is more varied, they may be [[Ionic compound|ionic]] or non-ionic, and can range from a simple or a relatively elaborate structure.<ref name=neugebauer>{{cite book |title=Detergents: An overview |series=Methods in Enzymology |volume= 182|year= 1990|pages= 239&ndash;253 |first=Judith M. |last=Neugebauer |chapter=&#91;18&#93; Detergents: An overview |doi=10.1016/0076-6879(90)82020-3 |pmid=2314239 |isbn=9780121820831 }}</ref> Detergents are surfactants since they can decrease the [[surface tension]] of water. Their dual nature facilitates the mixture of hydrophobic compounds (like oil and grease) with water. Because air is not hydrophilic, detergents are also [[foaming agent]]s to varying degrees.

[[File:Micelle scheme-en.svg|thumb|Structure of a micelle]]

Detergent molecules aggregate to form [[micelle]]s, which makes them soluble in water. The hydrophobic group of the detergent is the main driving force of micelle formation, its aggregation forms the hydrophobic core of the micelles. The micelle can remove grease, protein or soiling particles. The concentration at which micelles start to form is the [[critical micelle concentration]] (CMC), and the temperature at which the micelles further aggregate to separate the solution into two phases is the cloud point when the solution becomes cloudy and detergency is optimal.<ref name=neugebauer />

Detergents work better in an [[alkaline]] [[pH]]. The properties of detergents are dependent on the molecular structure of the [[monomer]]. The ability to foam may be determined by the head group, for example [[anionic surfactant]]s are high-foaming, while nonionic surfactants may be non-foaming or low-foaming.<ref>{{cite book|author=Niir Board |title=Handbook on Soaps, Detergents & Acid Slurry|url={{Google Books |vvQvDAAAQBAJ|page=270|plain-url=yes}}|date=1999|isbn=9788178330938|page=270 |publisher=Asia Pacific Business Press |via=Google Books|edition=3rd Revised }}</ref>

==Chemical classifications of detergents==
Detergents are classified into four broad groupings, depending on the electrical charge of the surfactants.<ref>{{cite book|editor=Guy Broze |first=Ammanuel |last=Mehreteab |title=Handbook of Detergents, Part A|url={{Google Books |iwsVEAAAQBAJ|page=133|plain-url=yes}}|date=1999|isbn=9781439833322|pages=133&ndash;134 |publisher=Taylor & Francis|via=Google Books}}</ref>

===Anionic detergents===
Typical anionic detergents are [[Sodium dodecylbenzenesulfonate|alkylbenzene sulfonates]]. The [[alkylbenzene]] portion of these [[anions]] is [[lipophilic]] and the sulfonate is [[hydrophilic]]. Two varieties have been popularized, those with branched [[alkyl group]]s and those with linear alkyl groups. The former were largely phased out in economically advanced societies because they are poorly biodegradable.<ref name=Ullmann>Eduard Smulders, Wolfgang Rybinski, Eric Sung, Wilfried Rähse, Josef Steber, Frederike Wiebel, Anette Nordskog, "Laundry Detergents" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a08_315.pub2}}</ref>

Anionic detergents are the most common form of detergents, and an estimated 6 billion kilograms of anionic detergents are produced annually for the domestic markets.

[[Bile acid]]s, such as [[deoxycholic acid]] (DOC), are anionic detergents produced by the liver to aid in digestion and absorption of fats and oils.

[[File:Soap&Detergents.png|thumb|480px|right|Three kinds of anionic detergents: a branched sodium dodecylbenzenesulfonate, linear [[sodium dodecylbenzenesulfonate]], and a soap.]]

===Cationic detergents===
Cationic detergents are similar to anionic ones, but [[quaternary ammonium]] replaces the hydrophilic anionic sulfonate group. The ammonium sulfate center is positively charged.<ref name=Ullmann/> Cationic surfactants generally have poor detergency.

===Non-ionic detergents===
Non-ionic detergents are characterized by their uncharged, hydrophilic headgroups. Typical non-ionic detergents are based on [[polyoxyethylene]] or a [[glycoside]]. Common examples of the former include [[polysorbate|Tween]], [[Triton X-100|Triton]], and the Brij series. These materials are also known as ethoxylates or PEGylates and their metabolites, [[nonylphenol]]. Glycosides have a sugar as their uncharged hydrophilic headgroup. Examples include [[n-Octyl beta-D-thioglucopyranoside|octyl thioglucoside]] and [[maltosides]]. HEGA and MEGA series detergents are similar, possessing a sugar alcohol as headgroup.

===Amphoteric detergents===
{{further|Surfactant#Applications and sources}}

[[Amphoterism|Amphoteric]] or zwitterionic detergents have [[zwitterion]]s within a particular pH range, and possess a net zero charge arising from the presence of equal numbers of +1 and −1 charged chemical groups. Examples include [[CHAPS detergent|CHAPS]].

==History==
{{see also|Soap#History}}

[[Soap]] is known to have been used as a surfactant for washing clothes since the [[Sumer|Sumerian]] time in 2,500 B.C.<ref name=falbe2>{{cite book|editor=Jürgen Falbe |title=Surfactants in Consumer Products|url={{Google Books |SjvtCAAAQBAJ|page=1|plain-url=yes}}|date=2012|publisher=Springer-Verlag|isbn=9783642715457|pages=1–2 |via=Google Books}}</ref> In [[ancient Egypt]], [[Sodium carbonate|soda]] was used as a wash additive. In the 19th century, synthetic surfactants began to be created, for example from olive oil.<ref name="sosis 5"/> [[Sodium silicate]] (water glass) was used in soap-making in the United States in the 1860s,<ref>{{cite book|first= Fred |last= Aftalion|title=A History of the International Chemical Industry|url={{Google Books |zTP1MFJw8CsC|page=82|plain-url=yes}}|date=2001|publisher=Chemical Heritage Press|isbn=9780941901291|page=82}}</ref> and in 1876, [[Henkel]] sold a sodium silicate-based product that can be used with soap and marketed as a "universal detergent" (''Universalwaschmittel'') in Germany. Soda was then mixed with sodium silicate to produce Germany's first brand name detergent Bleichsoda.<ref>{{cite book|first1=James |last1=Ward |date= 2020|last2= Löhr|title=The Perfection of the Paper Clip|url={{Google Books |q6_YDwAAQBAJ|page=190|plain-url=yes}}|publisher=Atria Books|isbn=9781476799872|page=190}}</ref> In 1907, Henkel also added a bleaching agent [[sodium perborate]] to launch the first 'self-acting' laundry detergent [[Persil]] to eliminate the laborious rubbing of laundry by hand.<ref>{{cite book|first1=Günter|last1= Jakobi |first2=Albrecht|last2= Löhr|title=Detergents and Textile Washing|url={{Google Books |is1TAAAAMAAJ|page=1|plain-url=yes}}|date=2012|publisher=Springer-Verlag|isbn=9780895736864|pages=3–4}}</ref>

During the [[World War I|First World War]], there was a shortage of oils and fats needed to make soap. In order to find alternatives for soap, synthetic detergents were made in Germany by chemists using raw material derived from coal tar.<ref>{{cite web|url=http://www.cleaninginstitute.org/clean_living/soaps__detergent_history_3.aspx|title=Soaps & Detergent: History (1900s to Now)|publisher=American Cleaning Institute}} Retrieved on 6 January 2015</ref><ref name="WhittenWhitten1997">{{cite book|author1=David O. Whitten|author2=Bessie Emrick Whitten|title=Handbook of American Business History: Extractives, manufacturing, and services|url={{Google Books |S-8god7-MlEC|page=221|plain-url=yes}}|date=1 January 1997|publisher=Greenwood Publishing Group|isbn=978-0-313-25199-3|pages=221–222 |via=Google Books}}</ref><ref name="sosis 5">{{cite book |url={{Google Books |dXn3aB1DKk4C|page=5|plain-url=yes}}|page=5 |title=Handbook of Detergents, Part F |editor =Paul Sosis, Uri Zoller |date= 2008 |publisher=CRC Press |isbn=9781420014655}}</ref> These early products, however, did not provide sufficient detergency. In 1928, effective detergent was made through the [[sulfation]] of [[fatty alcohol]], but large-scale production was not feasible until low-cost fatty alcohols become available in the early 1930s.<ref name=falbe /> The synthetic detergent created was more effective and less likely to form scum than soap in hard water, and can also eliminate acid and alkaline reactions and decompose dirt. Commercial detergent products with fatty alcohol sulphates began to be sold, initially in 1932 in Germany by [[Henkel]].<ref name=falbe /> In the United States, detergents were sold in 1933 by [[Procter & Gamble]] ([[Dreft]]) primarily in areas with hard water.<ref name="WhittenWhitten1997"/> However, sales in the US grew slowly until the introduction of 'built' detergents with the addition of effective [[Phosphates in detergent|phosphate builder]] developed in the early 1940s.<ref name="WhittenWhitten1997"/> The builder improves the performance of the surfactants by softening the water through the [[chelation]] of calcium and magnesium ions, helping to maintain an alkaline pH, as well as dispersing and keeping the soiling particles in solution.<ref>{{cite book |url={{Google Books |hctgblTQD-sC|page=4|plain-url=yes}}|pages=4–5 |title=How to Formulate and Compound Industrial Detergents |first= David G. |last=Urban |date= 2003 |publisher=David G. Urban |isbn=9781588988683}}</ref> The development of the petrochemical industry after the Second World War also yielded material for the production of a range of synthetic surfactants, and [[alkylbenzene sulfonate]]s became the most important detergent surfactants used.<ref name=handbook>{{cite book |url={{Google Books |dXn3aB1DKk4C|page=6|plain-url=yes}}|page=6 |title=Handbook of Detergents, Part F |editor =Paul Sosis, Uri Zoller |date= 2008 |publisher=CRC Press |isbn=9781420014655}}</ref> By the 1950s, [[laundry detergent]]s had become widespread, and largely replaced soap for cleaning clothes in developed countries.<ref name=falbe>{{cite book|editor=Jürgen Falbe |title=Surfactants in Consumer Products|url={{Google Books |SjvtCAAAQBAJ|page=4|plain-url=yes}}|date=2012|publisher=Springer-Verlag|isbn=9783642715457|pages=3–5 |via=Google Books}}</ref>

Over the years, many types of detergents have been developed for a variety of purposes, for example, low-sudsing detergents for use in front-loading washing machines, heavy-duty detergents effective in removing grease and dirt, all-purpose detergents and specialty detergents.<ref name="WhittenWhitten1997"/><ref>{{cite book |url={{Google Books |dXn3aB1DKk4C|page=497|plain-url=yes}}|page=497 |title=Handbook of Detergents, Part F |editor =Paul Sosis, Uri Zoller |date= 2008 |isbn=9781420014655}}</ref> They become incorporated in various products outside of laundry use, for example in [[dishwasher detergent]]s, shampoo, toothpaste, industrial cleaners, and in lubricants and fuels to reduce or prevent the formation of sludge or deposits.<ref>{{cite book |url={{Google Books |mCgcrvvRIucC|page=331|plain-url=yes}}|page=331 |title=Handbook of Detergents, Part E: Applications |editor=Uri Zoller |date= 2008 |publisher=Taylor & Francis|isbn=9781574447576}}</ref> The formulation of detergent products may include [[bleach]], fragrances, dyes and other additives. The use of [[phosphates in detergent]], however, led to concerns over [[nutrient pollution]] and demand for changes to the formulation of the detergents.<ref>{{cite book|author1=David O. Whitten|author2=Bessie Emrick Whitten|title=Handbook of Detergents, Part A|url={{Google Books |iwsVEAAAQBAJ|page=3|plain-url=yes}}|date=1999|publisher=Taylor & Francis|isbn=9781439833322|page=3 |via=Google Books}}</ref> Concerns were also raised over the use of surfactants such as branched alkylbenzene sulfonate (tetrapropylenebenzene sulfonate) that lingers in the environment, which led to their replacement by surfactants that are more biodegradable, such as linear alkylbenzene sulfonate.<ref name=falbe /><ref name=handbook /> Developments over the years have included the use of [[Detergent enzymes|enzymes]], substitutes for phosphates such as [[zeolite]] A and [[Nitrilotriacetic acid|NTA]], [[Tetraacetylethylenediamine|TAED]] as [[bleach activator]], sugar-based surfactants which are biodegradable and milder to skin, and other [[Environmentally friendly|green friendly]] products, as well as changes to the form of delivery such as tablets, gels and [[Laundry detergent pod|pods]].<ref name=Middelhauve>{{cite book |url={{Google Books |VMqSJROG_WYC|page=64|plain-url=yes}}|pages=64–67 |title=5th World Conference on Detergents |editor=Arno Cahn|first=Birgit |last= Middelhauve|date= 2003 |publisher=The American Oil Chemists Society |isbn=9781893997400}}</ref><ref>{{cite web |url= https://cleaning.lovetoknow.com/Laundry_Detergent_History |title=Laundry Detergent History|first= Heather |last=Long |work= Love to Know}}</ref>

==Major applications of detergents==
[[File:Laundry detergent pods.jpg|thumb|[[Laundry detergent pod]]s]]

===Household cleaning===
{{Main article|Laundry detergent|Dishwasher detergent}}

One of the largest applications of detergents is for household and shop cleaning including [[dish washing]] and washing [[laundry]]. These detergents are commonly available as powders or concentrated solutions, and the formulations of these detergents are often complex mixtures of a variety of chemicals aside from surfactants, reflecting the diverse demands of the application and the highly competitive consumer market. These detergents may contain the following components:<ref name=Middelhauve />
* [[surfactant]]s
* [[foam regulator]]s
* [[Builder (detergent)|builders]]
* [[bleach]]
* [[bleach activator]]s
* [[enzyme]]s
* dyes
* fragrances
* other additives

===Fuel additives===
Both carburetors and fuel injector components of [[internal combustion engine]]s benefit from detergents in the fuels to prevent [[fouling]]. Concentrations are about 300 [[parts per million#Parts-per expressions|ppm]]. Typical detergents are long-chain [[amine]]s and [[amide]]s such as [[polyisobuteneamine]] and polyisobuteneamide/[[succinimide]].<ref>Werner Dabelstein, Arno Reglitzky, Andrea Schütze, Klaus Reders "Automotive Fuels" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim{{doi|10.1002/14356007.a16_719.pub2}}</ref>

===Biological reagent===
[[chemical purity|Reagent grade]] detergents are employed for the isolation and purification of [[integral membrane proteins]] found in [[Cell_(biology)|biological cells]].<ref name="pmid20837548">{{cite journal |vauthors=Koley D, Bard AJ | title=Triton X-100 concentration effects on membrane permeability of a single HeLa cell by scanning electrochemical microscopy (SECM) | journal= [[Proceedings of the National Academy of Sciences of the United States of America]] | volume=107 | issue=39 | year=2010 | pages=16783–7 | doi=10.1073/pnas.1011614107 | pmc=2947864 | pmid=20837548| bibcode=2010PNAS..10716783K | doi-access=free }}</ref> Solubilization of [[cell membrane]] bilayers requires a detergent that can enter the inner membrane [[Monolayer#Biology|monolayer]].<ref name="pmid23870250">{{cite journal |vauthors=Lichtenberg D, Ahyayauch H, Goñi FM | title=The mechanism of detergent solubilization of lipid bilayers | journal= [[Biophysical Journal]] | volume=105 | issue=2 | year=2013 | pages=289–299 | doi=10.1016/j.bpj.2013.06.007 | pmc=3714928 | pmid=23870250| bibcode=2013BpJ...105..289L }}</ref> Advancements in the purity and sophistication of detergents have facilitated structural and biophysical characterization of important membrane proteins such as [[Ion channel|ion channels]] also the disrupt membrane by binding [[lipopolysaccharide]],<ref>{{cite journal | last1 = Doyle | first1 = DA | last2 = Morais Cabral | first2 = J | last3 = Pfuetzner | first3 = RA | last4 = Kuo | first4 = A | last5 = Gulbis | first5 = JM | last6 = Cohen | first6 = SL | last7 = Chait | first7 = BT | last8 = MacKinnon | first8 = R | year = 1998 | title = The structure of the potassium channel: molecular basis of K+conduction and selectivity | journal = Science | volume = 280 | issue = 5360| pages = 69–77 | doi=10.1126/science.280.5360.69 | pmid=9525859| bibcode = 1998Sci...280...69D }}</ref> [[Membrane transport protein|transporters]], [[Receptor (biochemistry)|signaling receptors]], and [[photosystem II]].<ref>{{cite journal | last1 = Umena | first1 = Yasufumi | last2 = Kawakami | first2 = Keisuke | last3 = Shen | first3 = Jian-Ren | last4 = Kamiya | first4 = Nobuo | year = 2011 | title = Crystal structure of oxygen-evolving photosystem II at a resolution of 1.9 A | url = http://ousar.lib.okayama-u.ac.jp/files/public/4/47455/20160528084139320094/Nature_473_55–60.pdf| journal = Nature | volume = 473 | issue = 7345| pages = 55–60 | doi = 10.1038/nature09913 | pmid=21499260| bibcode = 2011Natur.473...55U | s2cid = 205224374 }}</ref>

==See also==
* [[Cleavable detergent]]
* [[Dishwashing liquid]]
* [[Dispersant]]
* [[Green cleaning]]
* [[Hard-surface cleaner]]
* [[Laundry detergent]]
* [[List of cleaning products]]
* [[Triton X-100]]

==References==
{{reflist}}

==External links==
{{commons category|Detergents}}
* [http://chemistry.about.com/od/howthingswork/f/detergentfaq.htm About.com: How Do Detergents Clean] {{Webarchive|url=https://web.archive.org/web/20110106021626/http://chemistry.about.com/od/howthingswork/f/detergentfaq.htm |date=6 January 2011 }}
* [https://web.archive.org/web/20161119130839/http://www.chemistry.co.nz/deterginfo.htm Campbell tips] for detergents chemistry, [https://web.archive.org/web/20161129064828/http://www.chemistry.co.nz/surfactants.htm surfactants], and [https://web.archive.org/web/20161017172455/http://www.chemistry.co.nz/deterghistory.htm history] related to laundry washing, [https://web.archive.org/web/20161129092315/http://www.chemistry.co.nz/stain_frame.htm destaining methods] and [https://web.archive.org/web/20161018085331/http://www.chemistry.co.nz/soil_id.htm soil].
* {{usurped|1=[https://web.archive.org/web/20210519103618/https://laundrydetergentideas.com/formulation-of-detergent/ Formulation of Detergent]}}

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[[Category:Cleaning products]]
[[Category:Membrane-active molecules]]
[[Category:Surfactants]]
[[Category:Detergents| ]]