A monomer ( ; ''

mono- Numeral or number prefixes are prefixes derived from numerals or occasionally other numbers. In English and many other languages, they are used to coin numerous series of words. For example: * triangle, quadrilateral, pentagon, hexagon, oc ...

'', "one" + '' -mer'', "part") is a

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

that can react together with other monomer molecules to form a larger

polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...

chain or two- or three-dimensional network in a process called

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...

Classification

Chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

classifies monomers by type, and two broad classes based on the type of

they form. By type: * natural vs synthetic, e.g.

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (G ...

vs caprolactam, respectively * polar vs nonpolar, e.g.

vinyl acetate Vinyl acetate is an organic compound with the Chemical formula, formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers. Prod ...

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

, respectively * cyclic vs linear, e.g.

ethylene oxide Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless ...

vs ethylene glycol, respectively By type of polymer they form: * those that participate in condensation polymerization * those that participate in

addition polymerization Chain-growth polymerization ( AE) or chain-growth polymerisation ( BE) is a polymerization technique where monomer molecules add onto the active site on a growing polymer chain one at a time. There are a limited number of these active sites at an ...

Differing

stoichiometry Stoichiometry () is the relationships between the masses of reactants and Product (chemistry), products before, during, and following chemical reactions. Stoichiometry is based on the law of conservation of mass; the total mass of reactants must ...

causes each class to create its respective form of polymer. : The

of one kind of monomer gives a homopolymer. Many polymers are

copolymers In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are som ...

, meaning that they are derived from two different monomers. In the case of condensation polymerizations, the ratio of

comonomer In polymer chemistry, a comonomer refers to a polymerizable precursor to a copolymer aside from the principal monomer. In some cases, only small amounts of a comonomer are employed, in other cases substantial amounts of comonomers are used. Furt ...

s is usually 1:1. For example, the formation of many nylons requires equal amounts of a dicarboxylic acid and

diamine A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of ...

. In the case of addition polymerizations, the comonomer content is often only a few percent. For example, small amounts of 1-octene monomer are copolymerized with ethylene to give specialized polyethylene.

Synthetic monomers

Ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

gas (H₂C=CH₂) is the monomer for

polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including bott ...

. * Other modified ethylene derivatives include: **

tetrafluoroethylene Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula . It is a colorless gas. Its structure is . It is used primarily in the industrial preparation of fluoropolymers. It is the simplest perfluorinated alkene. It was first repor ...

(F₂C=CF₂) which leads to

Teflon Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene, and has numerous applications because it is chemically inert. The commonly known brand name of PTFE-based composition is Teflon by Chemours, a spin-off from ...

vinyl chloride Vinyl chloride is an organochloride with the formula H2C =CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. It is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). Vinyl chloride is a ...

(H₂C=CHCl) which leads to PVC **

styrene Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easi ...

(C₆H₅CH=CH₂) which leads to

polystyrene Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It i ...

Epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

monomers may be cross linked with themselves, or with the addition of a co-reactant, to form

epoxy Epoxy is the family of basic components or Curing (chemistry), cured end products of epoxy Resin, resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide fun ...

* BPA is the monomer precursor for

polycarbonate Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate ester, carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, toughness, tough materials, and some grades are optically transp ...

* Terephthalic acid is a comonomer that, with ethylene glycol, forms

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 ...

. * Dimethylsilicon dichloride is a monomer that, upon hydrolysis, gives

polydimethylsiloxane Polydimethylsiloxane (PDMS), also known as dimethylpolysiloxane or dimethicone, is a silicone polymer with a wide variety of uses, from cosmetics to industrial lubrication and passive daytime radiative cooling. PDMS is particularly known for its ...

. * Ethyl methacrylate is an acrylic monomer that, when combined with an acrylic polymer, catalyzes and forms an acrylate plastic used to create artificial nail extensions

Biopolymers

The term "monomeric

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...

" may also be used to describe one of the proteins making up a

multiprotein complex A protein complex or multiprotein complex is a group of two or more associated polypeptide chains. Protein complexes are distinct from multidomain enzymes, in which multiple catalytic domains are found in a single polypeptide chain. Protein c ...

Natural monomers

Some of the main

biopolymer Biopolymers are natural polymers produced by the cells of living organisms. Like other polymers, biopolymers consist of monomeric units that are covalently bonded in chains to form larger molecules. There are three main classes of biopolymers, ...

s are listed below:

Amino acids

For ''proteins'', the monomers are

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

s. Polymerization occurs at

ribosome Ribosomes () are molecular machine, macromolecular machines, found within all cell (biology), cells, that perform Translation (biology), biological protein synthesis (messenger RNA translation). Ribosomes link amino acids together in the order s ...

s. Usually about 20 types of amino acid monomers are used to produce proteins. Hence proteins are not homopolymers.

Nucleotides

For polynucleic acids (

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

RNA Ribonucleic acid (RNA) is a polymeric molecule that is essential for most biological functions, either by performing the function itself (non-coding RNA) or by forming a template for the production of proteins (messenger RNA). RNA and deoxyrib ...

), the monomers are

nucleotide Nucleotides are Organic compound, organic molecules composed of a nitrogenous base, a pentose sugar and a phosphate. They serve as monomeric units of the nucleic acid polymers – deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), both o ...

s, each of which is made of a pentose sugar, a nitrogenous base and a phosphate group. Nucleotide monomers are found in the

cell nucleus The cell nucleus (; : nuclei) is a membrane-bound organelle found in eukaryote, eukaryotic cell (biology), cells. Eukaryotic cells usually have a single nucleus, but a few cell types, such as mammalian red blood cells, have #Anucleated_cells, ...

. Four types of nucleotide monomers are precursors to DNA and four different nucleotide monomers are precursors to RNA.

Glucose and related sugars

For carbohydrates, the monomers are monosaccharides. The most abundant natural monomer is

glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...

, which is linked by glycosidic bonds into the polymers

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 ...

starch Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diet ...

, and

glycogen Glycogen is a multibranched polysaccharide of glucose that serves as a form of energy storage in animals, fungi, and bacteria. It is the main storage form of glucose in the human body. Glycogen functions as one of three regularly used forms ...

Isoprene

Isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers ar ...

is a natural monomer that polymerizes to form a

natural rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Types of polyisoprene ...

, most often ''cis-''1,4-polyisoprene, but also ''trans-''1,4-polymer.

Synthetic rubber A synthetic rubber is an artificial elastomer. They are polymers synthesized from petroleum byproducts. About of rubber is produced annually in the United States, and of that amount two thirds are synthetic. Synthetic rubber, just like natural ru ...

s are often based on butadiene, which is structurally related to isoprene.

Notes

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