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In
organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...
, a polyol is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
containing multiple
hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
s (). The term "polyol" can have slightly different meanings depending on whether it is used in
food science Food science (or bromatology) is the basic science and applied science of food; its scope starts at overlap with agricultural science and nutritional science and leads through the scientific aspects of food safety and food processing, informing ...
or
polymer chemistry Polymer chemistry is a sub-discipline of chemistry that focuses on the structures, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry are also applic ...
. Polyols containing two, three and four hydroxyl groups are
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
s,
triol In chemistry, a triol is an organic compound containing three hydroxyl groups ( functional groups),polyethylene oxide Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular we ...
or
polyethylene glycol Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular wei ...
(PEG),
polypropylene glycol Polypropylene glycol or polypropylene oxide is the polymer (or macromolecule) of propylene glycol. Chemically it is a polyether, and, more generally speaking, it's a polyalkylene glycol (PAG) H S Code 3907.2000. The term polypropylene glycol or PPG ...
(PPG) and
Polytetrahydrofuran Polytetrahydrofuran, also called poly(tetramethylene ether) glycol or poly(tetramethylene oxide), is a collection of chemical compounds with formula or HO((CH2)4O-)''n''-H. The material is a mixture of polyether diols terminated with alcohol gro ...
or PTMEG. These have 2, 3 and 4 carbons respectively per oxygen atom in the repeat unit. Polycaprolactone polyols are also commercially available. There is also an increasing trend to use biobased (and hence renewable) polyols.


Uses

Polyether polyols have numerous uses. As an example,
polyurethane foam Polyurethane foam is a solid polymeric foam based on polyurethane chemistry. As a specialist synthetic fibre, synthetic material with highly diverse applications, polyurethane foams are primarily used for thermal insulation and as a cushioning mat ...
is a big user of polyether polyols. Polyester polyols can be used to produce rigid foam. They are available in both
aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
and
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
versions. They are also available in mixed aliphatic-aromatic versions often made from recycled raw materials, typically
polyethylene terephthalate Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in synthetic fibre, fibres for clothing, packaging, conta ...
(PET). Acrylic polyols are generally used in higher performance applications where stability to
ultraviolet Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...
light is required and also lower
VOC VOC, VoC or voc may refer to: Science and technology * Open-circuit voltage (VOC), the voltage between two terminals when there is no external load connected * Variant of concern, a category used during the assessment of a new variant of a virus * ...
coatings. Other uses include direct to metal coatings. As they are used where good UV resistance is required, such as automotive coatings, the
isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...
component also tends to be UV resistant and hence isocyanate oligomers or
prepolymer In polymer chemistry, the term prepolymer or pre-polymer, refers to a monomer or system of monomers that have been reacted to an intermediate-molecular mass state. This material is capable of further polymerization by reactive groups to a fully c ...
s based on
Isophorone diisocyanate Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an Aliphatic compound, aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diis ...
are generally used. Caprolactone-based polyols produce polyurethanes with enhanced hydrolysis resistance. Polycarbonate polyols are more expensive than other polyols and are thus used in more demanding applications. They have been used to make an
isophorone diisocyanate Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an Aliphatic compound, aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diis ...
based prepolymer which is then used in glass coatings. They may be used in reactive hotmelt
adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...
s. All polyols may be used to produce polyurethane
prepolymer In polymer chemistry, the term prepolymer or pre-polymer, refers to a monomer or system of monomers that have been reacted to an intermediate-molecular mass state. This material is capable of further polymerization by reactive groups to a fully c ...
s. These then find use in
coatings A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints and ...
,
adhesives Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...
,
sealants Sealant is a substance used to block the passage of fluids through openings in materials, a type of mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulk'' (especially if acrylic latex or polyurethane based ...
and
elastomers An elastomer is a polymer with viscoelasticity (i.e. both viscosity and Elasticity (physics), elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a ...
.


Low molecular weight polyols

Low molecular weight polyols are widely used in
polymer chemistry Polymer chemistry is a sub-discipline of chemistry that focuses on the structures, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry are also applic ...
where they function as crosslinking agents and chain extenders.
Alkyd resin An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term ''alkyd'' is ...
s for example, use polyols in their synthesis and are used in
paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...
s and in molds for
casting Casting is a manufacturing process in which a liquid material is usually poured into a mold, which contains a hollow cavity of the desired shape, and then allowed to solidify. The solidified part is also known as a casting, which is ejected or ...
. They are the dominant
resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...
or "binder" in most commercial "oil-based" coatings. Approximately 200,000 tons of alkyd resins are produced each year. They are based on linking reactive monomers through ester formation. Polyols used in the production of commercial alkyd resins are
glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
,
trimethylolpropane 300 C--> Trimethylolpropane (TMP) is the organic compound with the formula CH3CH2C(CH2OH)3. This colourless to white solid with a faint odor is a triol. Containing three hydroxy functional groups, TMP is a widely used building block in the polymer ...
, and
pentaerythritol Pentaerythritol is an organic compound with the formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a ...
. In polyurethane prepolymer production, a low molecular weight polyol-
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
such as 1,4-butanediol may be used as a chain extender to further increase molecular weight though it does increase
viscosity Viscosity is a measure of a fluid's rate-dependent drag (physics), resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for e ...
because more
hydrogen bonding In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
is introduced.


Sugar alcohols

Sugar alcohol Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group attached to each carbon atom. They are white, water-soluble solids that c ...
s, a class of low molecular weight polyols, are commonly obtained by
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
of sugars. They have the formula (CHOH)nH2, where n = 4–6. Sugar alcohols are added to foods because of their lower caloric content than
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecul ...
s; however, they are also, in general, less sweet, and are often combined with high-intensity
sweeteners A sweetener is a substance added to food or drink to impart the flavor of sweetness, either because it contains a type of sugar, or because it contains a sweet-tasting sugar substitute. Various natural non-sugar sweeteners (NSS) and artificial s ...
. They are also added to
chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its tex ...
because they are not broken down by bacteria in the mouth or
metabolized Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
to acids, and thus do not contribute to
tooth decay Tooth decay, also known as caries,The word 'caries' is a mass noun, and is not a plural of 'carie'.'' is the breakdown of teeth due to acids produced by bacteria. The resulting cavities may be a number of different colors, from yellow to black ...
.
Maltitol Maltitol is a sugar alcohol (a polyol) used as a sugar substitute and laxative. It has 75–90% of the sweetness of sucrose (table sugar) and nearly identical properties, except for browning. It is used to replace table sugar because it is hal ...
,
sorbitol Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alco ...
,
xylitol Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular Stereoisomerism, stereoisomer with that structural formula. It is a colorless or white crystalline solid. It is classified as a polyalcoho ...
,
erythritol Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a food ad ...
, and isomalt are common sugar alcohols.


Polymeric polyols

The term ''polyol'' is used for various chemistries of the molecular backbone. Polyols may be reacted with
diisocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...
s or polyisocyanates to produce
polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...
s. MDI finds considerable use in PU foam production. Polyurethanes are used to make flexible foam for
mattresses A mattress is a large, usually rectangular pad for supporting a person Lying (position), lying down, especially for sleeping. It is designed to be used as a bed, or on a bed frame as part of a bed. Mattresses may consist of a Quilting, quilted o ...
and seating, rigid foam insulation for
refrigerator A refrigerator, commonly shortened to fridge, is a commercial and home appliance consisting of a thermal insulation, thermally insulated compartment and a heat pump (mechanical, electronic or chemical) that transfers heat from its inside to ...
s and freezers,
elastomeric An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a portmanteau of ''elas ...
shoe soles, fibers (e.g.
Spandex Spandex, Lycra, or elastane is a synthetic fiber known for its exceptional elasticity. It is a polyether- polyurea copolymer that was invented in 1958 by chemist Joseph Shivers at DuPont. Name The name ''spandex'', which is an anagram of t ...
), coatings, sealants and
adhesives Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...
. The term ''polyol'' is also attributed to other molecules containing hydroxyl groups. For instance,
polyvinyl alcohol Polyvinyl alcohol (PVOH, PVA, or PVAl) is a water- soluble synthetic polymer. It has the idealized formula H2CH(OH)sub>''n''. It is used in papermaking, textile warp sizing, as a thickener and emulsion stabilizer in polyvinyl acetate (PVAc) a ...
is (CH2CHOH)''n'' with ''n'' hydroxyl groups where ''n'' can be in the thousands.
Cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...
is a polymer with many hydroxyl groups, but it is not referred to as a polyol.


Polyols from recycled or renewable sources

There are polyols based on renewable sources such as
plant-based A plant-based diet is a diet consisting mostly or entirely of plant-based foods. It encompasses a wide range of dietary patterns that contain low amounts of animal products and high amounts of fiber-rich plant products such as vegetables, ...
materials including
castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...
and
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. cottonseed, Cotton seed has a similar structure to ...
. Vegetable oils and biomass are also potential renewable polyol raw materials. Seed oil can even be used to produce polyester polyols.


Properties

Since the generic term polyol is only derived from
chemical nomenclature Chemical nomenclature is a set of rules to generate systematic name#In chemistry, systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Appli ...
and just indicates the presence of several hydroxyl groups, no common properties can be assigned to all polyols. However, polyols are usually viscous at room temperature due to hydrogen bonding.


See also

*
Cyclitol In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is or where 3 ≤ ''x'' ≤ ''n''. The name is also used for ...
*
Oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
*
Polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...


References


External links

*{{Commons category-inline, Polyols Sugar substitutes Organic polymers Commodity chemicals Polymer chemistry Synthetic resins Polyurethanes