Polyol
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In
organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J ...
, a polyol is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
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 or
polymer chemistry Polymer chemistry is a sub-discipline of chemistry that focuses on the structures of chemicals, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry ar ...
. Polyols containing two, three and four hydroxyl groups are
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...
s, triols, and tetrols, respectively.


Classification

Polyols may be classified according to their chemistry. Some of these chemistries are polyether, polyester, polycarbonate and also acrylic polyols. Polyether polyols may be further subdivided and classified as polyethylene oxide 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 we ...
(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 PP ...
(PPG) and Polytetrahydrofuran 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 is a big user of polyether polyols. Polyester polyols can be used to produce rigid foam. They are available in both aromatic and aliphatic versions. In addition 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 fibres for clothing, containers for liquids and food ...
(PET). Acrylic polyols are generally used in higher performance applications where stability to
Ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30  PHz) to 400 nm (750  THz), shorter than that of visible light, but longer than X-rays. UV radiation ...
light is required and also lower VOC coatings. Other uses include direct to metal coatings. As they are used where good UV resistance is required, such as automotive coatings, the isocyanate component also tends to be UV resistant and hence isocyanate oligomers or prepolymers based on Isophorone diisocyanate 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 based prepolymer which is then used in glass coatings. They maybe 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 advant ...
s. All polyols maybe used to produce polyurethane prepolymers. These then find use in coatings,
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 advant ...
, sealants and elastomers.


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 of chemicals, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry ar ...
where they function as crosslinking agents and chain extenders. Alkyd resins for example, use polyols in their synthesis and are used in
paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
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 ejecte ...
. They are the dominant
resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on nat ...
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 (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
, trimethylolpropane, and pentaerythritol. In polyurethane prepolymer production, a low molecular weight polyol-
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...
such as 1,4-Butanediol maybe used as a chain extender to further increase molecular weight though it does increase
viscosity The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the int ...
because more hydrogen bonding 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 (–OH) attached to each carbon atom. They are white, water-soluble solids ...
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 reduce or saturate organic ...
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, fructose, and galactose. Compound sugars, also called disaccharides or do ...
s; however, they are also, in general, less sweet, and are often combined with high-intensity sweeteners. 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 t ...
because they are not broken down by bacteria in the mouth or
metabolized Metabolism (, from el, μεταβολή ''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 cell ...
to acids, and thus do not contribute to tooth decay. Maltitol,
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 alcoho ...
, xylitol,
erythritol Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula is ...
, 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 diisocyanates or polyisocyanates to produce
polyurethane Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...
s. MDI finds considerable use in PU foam production. Polyurethanes are used to make flexible foam for mattresses and seating, rigid foam insulation for
refrigerator A refrigerator, colloquially fridge, is a commercial and home appliance consisting of a thermally insulated compartment and a heat pump (mechanical, electronic or chemical) that transfers heat from its inside to its external environment so th ...
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 and high failure strain compared with other materials. The term, a portmanteau of ''elast ...
shoe soles, fibers (e.g. Spandex), 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 advant ...
. The term "polyol" is also attributed to other molecules containing hydroxyl groups. For instance,
polyvinyl alcohol Poly(vinyl 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) ...
is (CH2CHOH)''n'' with ''n'' hydroxyl groups where ''n'' can be in the thousands.
Cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wa ...
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 materials including
castor oil Castor oil is a vegetable oil pressed from castor beans. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about ...
. Vegetable oils and biomass are also potential renewable polyol raw materials.


Properties

Since the generic term polyol is only derived from
chemical nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). Th ...
and just indicates the presence of several hydroxyl groups, no common properties can be assigned to all polyols. However, polyols are usually highly viscous (when polymeric) to solid (when low-molecular weight) 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 c ...
*
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 relati ...
*
Polyurethane Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...


References


External links

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