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 ...
, vinyl polymers are a group of
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 ...
s derived from substituted
vinyl
Vinyl may refer to:
Chemistry
* Polyvinyl chloride (PVC), a particular vinyl polymer
* Vinyl cation, a type of carbocation
* Vinyl group, a broad class of organic molecules in chemistry
* Vinyl polymer, a group of polymers derived from vinyl ...
()
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 ...
s. Their
backbone is an extended
alkane
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
chain .
In popular usage, "vinyl" refers only to
polyvinyl chloride
Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
(PVC).
Examples
Vinyl polymers are the most common type of plastic. Important examples can be distinguished by the R group in the monomer H
2C=CHR:
*
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 ...
R = H
*
polypropylene
Polypropylene (PP), also known as polypropene, is a thermoplastic polymer used in a wide variety of applications. It is produced via chain-growth polymerization from the monomer Propene, propylene.
Polypropylene belongs to the group of polyolefin ...
from
propylene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like o ...
, R = CH
3
*
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 ...
is made from
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 ...
, R = C
6H
5
*
Polyvinyl chloride
Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
(PVC) is made 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 ...
, R= Cl
*
Polyvinyl acetate (PVAc) is made from
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 ...
, R = O
2CCH
3
*
Polyacrylonitrile
Polyacrylonitrile (PAN) is a synthetic, semicrystalline organic polymer resin, with the linear formula (CH2CHCN)n. Almost all PAN resins are copolymers with acrylonitrile as the main monomer. PAN is used to produce large variety of products in ...
is made from
acrylonitrile, R = CN
:
Production
Vinyl polymers are produced using catalysts.
Ziegler–Natta catalyst
A Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, is a catalyst used in the synthesis of polymers of 1-alkenes ( alpha-olefins). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility ...
s are used commercially for production of polyethylene and polypropylene. Many are produced using radical initiators which are produced from
organic peroxide
In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group (). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily b ...
s. Still others (polystyrene) are produced using anionic initiators such as
butyl lithium.
An exception from the usual rules,
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 ...
, )
n, is produced by hydrolysis of polyvinyl acetate. Vinyl alcohol is not sufficiently stable to undergo polymerization.
Structure
Vinyl polymers are subject of several structural variations, which greatly expands the range of polymers and their applications.
With the exception of polyethylene, vinyl polymers can arise from head-to-tail linking of monomers, head-to-head combined with tail-to-tail, or a mixture of those two patterns. Additionally the substituted carbon center in such polymers is
stereogenic
In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups cr ...
(a "chiral center"), with the result that the relative
absolute configuration
In chemistry, absolute configuration refers to the spatial arrangement of atoms within a molecular entity (or Functional group, group) that is chirality (chemistry), chiral, and its resultant stereochemical description. Absolute configuration is ...
s of these centers within a polymer can influence the properties of the polymer. This feature is called
tacticity. The polymerization conditions and the catalysts affect tacticity.
Another major variation for vinyl polymers arises from the copolymerization of differing vinyl monomers. The simplest example is ethylene-propylene copolymer. The %
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 ...
is yet another variation.
See also
*
Acrylate polymer
An acrylate polymer (also known as acrylic or polyacrylate) is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.
Acrylate polymer is commonly used ...
References
{{Authority control
Organic polymers