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A detergent is a
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
or a
mixture In chemistry, a mixture is a material made up of two or more different chemical substances which can be separated by physical method. It is an impure substance made up of 2 or more elements or compounds mechanically mixed together in any proporti ...
of surfactants with cleansing properties when in dilute
solutions Solution may refer to: * Solution (chemistry), a mixture where one substance is dissolved in another * Solution (equation), in mathematics ** Numerical solution, in numerical analysis, approximate solutions within specified error bounds * Solutio ...
. There are a large variety of detergents. A common family is the
alkylbenzene sulfonates Alkylbenzene sulfonates are a class of anionic surfactants, consisting of a hydrophilic sulfonate head-group and a hydrophobic alkylbenzene tail-group. Along with sodium laureth sulfate, they are one of the oldest and most widely used synthetic ...
, which are
soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
-like compounds that are more soluble than soap in
hard water Hard water is water that has a high mineral content (in contrast with "soft water"). Hard water is formed when water percolates through deposits of limestone, chalk or gypsum, which are largely made up of calcium and magnesium carbonates, bic ...
, because the polar
sulfonate In organosulfur chemistry, a sulfonate is a salt, anion or ester of a sulfonic acid. Its formula is , containing the functional group , where R is typically an organyl group, amino group or a halogen atom. Sulfonates are the conjugate bases of ...
is less likely than the polar
carboxylate In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an anion, an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,... ...
of soap to bind to calcium and other ions found in hard water.


Definitions

The word ''detergent'' is derived from the
Latin Latin ( or ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...
adjective , from the verb , meaning to wipe or polish off. Detergent can be defined as a
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
or a
mixture In chemistry, a mixture is a material made up of two or more different chemical substances which can be separated by physical method. It is an impure substance made up of 2 or more elements or compounds mechanically mixed together in any proporti ...
of surfactants with cleansing properties when in dilute
solutions Solution may refer to: * Solution (chemistry), a mixture where one substance is dissolved in another * Solution (equation), in mathematics ** Numerical solution, in numerical analysis, approximate solutions within specified error bounds * Solutio ...
. However, conventionally, detergent is used to mean synthetic cleaning compounds as opposed to ''
soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
'' (a salt of the natural
fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
), even though soap is also a detergent in the true sense. In domestic contexts, the term ''detergent'' refers to household cleaning products such as ''
laundry detergent Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form. While powdered and liquid detergents hold roughly equal share of ...
'' or '' 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).


Structure and properties

Detergents are a group of compounds with an
amphiphilic In chemistry, an amphiphile (), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'', nonpolar) properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic c ...
structure, where each molecule has a
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...
(polar) head and a long
hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...
(non-polar) tail. The hydrophobic portion of these molecules may be straight- or branched-chain
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
s, or it may have a
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
structure. The hydrophilic portion is more varied, they may be ionic or non-ionic, and can range from a simple or a relatively elaborate structure. Detergents are surfactants since they can decrease the
surface tension Surface tension is the tendency of liquid surfaces at rest to shrink into the minimum surface area possible. Surface tension (physics), tension is what allows objects with a higher density than water such as razor blades and insects (e.g. Ge ...
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 A foaming agent is a material such as a surfactant or a blowing agent that facilitates the formation of foam. A surfactant, when present in small amounts, reduces surface tension of a liquid (reduces the work needed to create the foam) or increas ...
s to varying degrees. Detergent molecules aggregate to form
micelle A micelle () or micella () ( or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension (also known as associated colloidal system). ...
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 In colloidal chemistry, colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles. The ...
(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. Detergents work better in an
alkaline In chemistry, an alkali (; from the Arabic word , ) is a basic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a soluble base has a pH greater than 7.0. The ...
pH. The properties of detergents are dependent on the molecular structure of the
monomer A monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called polymerization. Classification Chemis ...
. The ability to foam may be determined by the head group, for example
anionic surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
s are high-foaming, while nonionic surfactants may be non-foaming or low-foaming.


Chemical classifications of detergents

Detergents are classified into four broad groupings, depending on the electrical charge of the surfactants.


Anionic detergents

Typical anionic detergents are
alkylbenzene sulfonates Alkylbenzene sulfonates are a class of anionic surfactants, consisting of a hydrophilic sulfonate head-group and a hydrophobic alkylbenzene tail-group. Along with sodium laureth sulfate, they are one of the oldest and most widely used synthetic ...
. The alkylbenzene portion of these
anions An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
is
lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
and the sulfonate is
hydrophilic A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press. In contrast, hydrophobes are n ...
. Two varieties have been popularized, those with branched
alkyl group In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...
s and those with linear alkyl groups. The former were largely phased out in economically advanced societies because they are poorly biodegradable.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. 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 Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver in peroxisomes. Bile acids are conjugated with taurine or glycine residues to give anions called bile ...
s, such as deoxycholic acid (DOC), are anionic detergents produced by the liver to aid in digestion and absorption of fats and oils.


Cationic detergents

Cationic detergents are similar to anionic ones, but
quaternary ammonium In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, o ...
replaces the hydrophilic anionic sulfonate group. The ammonium sulfate center is positively charged. 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 In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
. Common examples of the former include Tween, Triton, and the Brij series. These materials are also known as ethoxylates or PEGylates and their metabolites,
nonylphenol Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, l ...
. Glycosides have a sugar as their uncharged hydrophilic headgroup. Examples include octyl thioglucoside and maltosides. HEGA and MEGA series detergents are similar, possessing a sugar alcohol as headgroup.


Amphoteric detergents

Amphoteric In chemistry, an amphoteric compound () is a molecule or ion that can react both as an acid and as a base. What exactly this can mean depends on which definitions of acids and bases are being used. Etymology and terminology Amphoteric is d ...
or zwitterionic detergents have
zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively and negatively charged functional groups. : (1,2- dipolar compounds, such as ylides, are sometimes excluded from ...
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 Chaparreras or chaps () are a type of sturdy over-pants (overalls) or leggings of Mexican origin, made of leather, without a seat, made up of two separate legs that are fastened to the waist with straps or belt. They are worn over trousers and ...
.


History

Soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...
is known to have been used as a surfactant for washing clothes since the Sumerian time in 2,500 B.C. In
ancient Egypt Ancient Egypt () was a cradle of civilization concentrated along the lower reaches of the Nile River in Northeast Africa. It emerged from prehistoric Egypt around 3150BC (according to conventional Egyptian chronology), when Upper and Lower E ...
, soda was used as a wash additive. In the 19th century, synthetic surfactants began to be created, for example from olive oil.
Sodium silicate Sodium silicate is a generic name for chemical compounds with the formula or ·, such as sodium metasilicate (), sodium orthosilicate (), and sodium pyrosilicate (). The anions are often polymeric. These compounds are generally colorless tra ...
(water glass) was used in soap-making in the United States in the 1860s, and in 1876,
Henkel Henkel AG & Co. KGaA, commonly known as Henkel, is a German multinational chemical and consumer goods company headquartered in Düsseldorf, Germany. Founded in 1876, the DAX company is organized into two globally operating business units (Cons ...
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. In 1907, Henkel also added a bleaching agent
sodium perborate Sodium perborate are chemical compounds with chemical formula (H2O)x. Commonly encountered salts are the anhydrous form (x = 0) and as a hydrate, hexahydrate (x = 6). These two species are sometimes called, respectively, "monohydrate" or PBS-1 a ...
to launch the first 'self-acting' laundry detergent
Persil Persil (, ) is a German brand of laundry detergent manufactured and marketed by Henkel around the world except in the United Kingdom, Ireland, France, Latin America (except Mexico), China, Australia and New Zealand, where it is manufactured an ...
to eliminate the laborious rubbing of laundry by hand. During the
First World War World War I or the First World War (28 July 1914 – 11 November 1918), also known as the Great War, was a World war, global conflict between two coalitions: the Allies of World War I, Allies (or Entente) and the Central Powers. Fighting to ...
, 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. These early products, however, did not provide sufficient detergency. In 1928, effective detergent was made through the
sulfation Sulfation (sometimes spelled sulphation in British English) is the chemical reaction that entails the addition of SO3 group. In principle, many sulfations would involve reactions of sulfur trioxide (SO3). In practice, most sulfations are effected ...
of
fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...
, but large-scale production was not feasible until low-cost fatty alcohols become available in the early 1930s. 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 Henkel AG & Co. KGaA, commonly known as Henkel, is a German multinational chemical and consumer goods company headquartered in Düsseldorf, Germany. Founded in 1876, the DAX company is organized into two globally operating business units (Cons ...
. In the United States, detergents were sold in 1933 by
Procter & Gamble The Procter & Gamble Company (P&G) is an American multinational consumer goods corporation headquartered in Cincinnati, Ohio. It was founded in 1837 by William Procter and James Gamble. It specializes in a wide range of personal health/con ...
( Dreft) primarily in areas with hard water. However, sales in the US grew slowly until the introduction of 'built' detergents with the addition of effective phosphate builder developed in the early 1940s. The builder improves the performance of the surfactants by softening the water through the
chelation Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...
of calcium and magnesium ions, helping to maintain an alkaline pH, as well as dispersing and keeping the soiling particles in solution. 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 sulfonates became the most important detergent surfactants used. By the 1950s,
laundry detergent Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form. While powdered and liquid detergents hold roughly equal share of ...
s had become widespread, and largely replaced soap for cleaning clothes in developed countries. 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. They become incorporated in various products outside of laundry use, for example in dishwasher detergents, shampoo, toothpaste, industrial cleaners, and in lubricants and fuels to reduce or prevent the formation of sludge or deposits. The formulation of detergent products may include
bleach Bleach is the generic name for any chemical product that is used industrially or domestically to remove color from (i.e. to whiten) fabric or fiber (in a process called bleaching) or to disinfect after cleaning. It often refers specifically t ...
, fragrances, dyes and other additives. The use of phosphates in detergent, however, led to concerns over
nutrient pollution Nutrient pollution is a form of water pollution caused by too many Nutrient, nutrients entering the water. It is a primary cause of eutrophication of surface waters (lakes, rivers and Coast, coastal waters), in which excess nutrients, usually ni ...
and demand for changes to the formulation of the detergents. 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. Developments over the years have included the use of
enzymes An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as pro ...
, substitutes for phosphates such as
zeolite Zeolites are a group of several microporous, crystalline aluminosilicate minerals commonly used as commercial adsorbents and catalysts. They mainly consist of silicon, aluminium, oxygen, and have the general formula ・y where is either a meta ...
A and NTA, TAED as bleach activator, sugar-based surfactants which are biodegradable and milder to skin, and other green friendly products, as well as changes to the form of delivery such as tablets, gels and pods.


Major applications of detergents


Household cleaning

One of the largest applications of detergents is for household and shop cleaning including dish washing and washing
laundry Laundry is the washing of clothing and other textiles, and, more broadly, their drying and ironing as well. Laundry has been part of history since humans began to wear clothes, so the methods by which different cultures have dealt with this u ...
. 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: *
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
s * foam regulators * builders *
bleach Bleach is the generic name for any chemical product that is used industrially or domestically to remove color from (i.e. to whiten) fabric or fiber (in a process called bleaching) or to disinfect after cleaning. It often refers specifically t ...
* bleach activators *
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s * dyes * fragrances * other additives


Fuel additives

Both carburetors and fuel injector components of
internal combustion engine An internal combustion engine (ICE or IC engine) is a heat engine in which the combustion of a fuel occurs with an oxidizer (usually air) in a combustion chamber that is an integral part of the working fluid flow circuit. In an internal comb ...
s benefit from detergents in the fuels to prevent
fouling Fouling is the accumulation of unwanted material on solid surfaces. The fouling materials can consist of either living organisms (biofouling, organic) or a non-living substance (inorganic). Fouling is usually distinguished from other surfac ...
. Concentrations are about 300 ppm. Typical detergents are long-chain
amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s and
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
s such as polyisobuteneamine and polyisobuteneamide/
succinimide Succinimide is an organic compound with the formula (CH2)2(CO)2NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic imide. It may be prepared ...
.


Biological reagent

Reagent grade detergents are employed for the isolation and purification of
integral membrane proteins An integral, or intrinsic, membrane protein (IMP) is a type of membrane protein that is permanently attached to the biological membrane. All transmembrane proteins can be classified as IMPs, but not all IMPs are transmembrane proteins. IMPs com ...
found in biological cells. Solubilization of
cell membrane The cell membrane (also known as the plasma membrane or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of a cell from the outside environment (the extr ...
bilayers requires a detergent that can enter the inner membrane
monolayer A monolayer is a single, closely packed layer of entities, commonly atoms or molecules. Monolayers can also be made out of cells. ''Self-assembled monolayers'' form spontaneously on surfaces. Monolayers of layered crystals like graphene and molyb ...
. Advancements in the purity and sophistication of detergents have facilitated structural and biophysical characterization of important membrane proteins such as
ion channels Ion channels are pore-forming membrane proteins that allow ions to pass through the channel pore. Their functions include establishing a resting membrane potential, shaping action potentials and other electrical signals by gating the flow of ...
also the disrupt membrane by binding
lipopolysaccharide Lipopolysaccharide (LPS), now more commonly known as endotoxin, is a collective term for components of the outermost membrane of the cell envelope of gram-negative bacteria, such as '' E. coli'' and ''Salmonella'' with a common structural archit ...
, transporters, signaling receptors, and
photosystem II Photosystem II (or water-plastoquinone oxidoreductase) is the first protein complex in the light-dependent reactions of oxygenic photosynthesis. It is located in the thylakoid membrane of plants, algae, and cyanobacteria. Within the photosystem ...
.


See also

* Cleavable detergent *
Dishwashing liquid Dishwashing liquid (washing-up liquid or fairy liquid in British English), also known as dishwashing soap, dish detergent, or dish soap, is a detergent used in dishwashing. Dishwashing detergent for dishwashers comes in various forms such a ...
*
Dispersant A dispersant or a dispersing agent is a substance, typically a surfactant, that is added to a suspension of solid or liquid particles in a liquid (such as a colloid or emulsion) to improve the separation of the particles and to prevent their sett ...
* Green cleaning * Hard-surface cleaner *
Laundry detergent Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form. While powdered and liquid detergents hold roughly equal share of ...
* List of cleaning products *
Triton X-100 Triton X-100 (''n'') is a nonionic surfactant that has a hydrophilic polyethylene oxide chain (on average it has 9.5 ethylene oxide units) and an aromatic hydrocarbon lipophilic or hydrophobic group. The hydrocarbon group is a 4-( 1,1,3,3-tetr ...


References


External links


About.com: How Do Detergents Clean


for detergents chemistry

an

related to laundry washing

an

* {{Authority control Cleaning products Membrane-active molecules Surfactants