Cyclic Olefin Copolymer
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Cyclic olefin copolymer (COC) is an amorphous polymer made by several polymer manufacturers. COC is a relatively new class of polymers as compared to commodities such as
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 propylene. Polypropylene belongs to the group of polyolefins and ...
and
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 bo ...
. This newer material is used in a wide variety of applications including packaging films, lenses, vials, displays, and medical devices.


Various types

In 2005 there were "several types of commercial cyclic olefin copolymers based on different types of cyclic monomers and polymerization methods. Cyclic olefin copolymers are produced by chain copolymerization of cyclic monomers such as 8,9,10-trinorborn-2-ene (
norbornene Norbornene or norbornylene or norcamphene is a highly strained bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carr ...
) or 1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (tetracyclododecene) with
ethene 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 double bonds). Ethylene is ...
(such as Polyplastics subsidiary TOPAS Advanced Polymers' TOPAS, Mitsui Chemical's APEL), or by
ring-opening metathesis polymerization Ring-opening metathesis polymerization (ROMP) is a type of olefin metathesis chain-growth polymerization. The driving force of the reaction is relief of ring strain in cyclic olefins (e.g. norbornene or cyclopentene). A variety of heterogeneous ...
of various cyclic monomers followed by hydrogenation (Japan Synthetic Rubber's ARTON, Zeon Chemical's Zeonex and Zeonor)." These later materials using a single type of monomer are more properly named cyclic olefin polymers (COP).


Chemical and physical properties

Typical COC material has a higher modulus than
HDPE High-density polyethylene (HDPE) or polyethylene high-density (PEHD) is a thermoplastic polymer produced from the monomer ethylene. It is sometimes called "alkathene" or "polythene" when used for HDPE pipes. With a high strength-to-density ratio, ...
and PP, similar to
PET A pet, or companion animal, is an animal kept primarily for a person's company or entertainment rather than as a working animal, livestock, or a laboratory animal. Popular pets are often considered to have attractive appearances, intelligence, ...
or PC. COC also has a high moisture barrier for a clear polymer along with a low moisture absorption rate. In medical and analytical applications, COC is noted to be a high purity product with low extractables. COC is also a
halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...
-free and BPA-free product. Some grades of COC have shown a lack of
estrogenic Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal activ ...
activity.{{Cite journal , title=Yang et al (July 2011), "Most Plastic Products Release Estrogenic Chemicals: A Potential Health Problem That Can Be Solved" ''Environmental Health Perspectives'' , year=2011 , doi=10.1289/ehp.1003220 , pmid=21367689 , s2cid=18809650 , last1=Yang , first1=C. Z. , last2=Yaniger , first2=S. I. , last3=Jordan , first3=V. C. , last4=Klein , first4=D. J. , last5=Bittner , first5=G. D. , journal=Environmental Health Perspectives , volume=119 , issue=7 , pages=989–996 , pmc=3222987 The optical properties of COC are exceptional, and in many ways very similar to glass. COC materials offer exceptional transparency, low
birefringence Birefringence is the optical property of a material having a refractive index that depends on the polarization and propagation direction of light. These optically anisotropic materials are said to be birefringent (or birefractive). The birefring ...
, high
Abbe number In optics and lens design, the Abbe number, also known as the V-number or constringence of a transparent material, is an approximate measure of the material's dispersion (change of refractive index versus wavelength), with high values of ''V'' ind ...
and high heat resistance. The moisture insensitivity of COC is often an advantage over competing materials such as polycarbonate and acrylics. The high flow of COC enables higher aspect ratio (squatter and shallower) optical component fabrication than other optical polymers. High ultraviolet transmission is a hallmark of COC materials, with optimized grades the leading polymer alternatives to quartz glass in analytical and diagnostic applications. Some properties vary due to monomer content. These include
glass transition temperature The glass–liquid transition, or glass transition, is the gradual and reversible transition in amorphous materials (or in amorphous regions within semicrystalline materials) from a hard and relatively brittle "glassy" state into a viscous or rubb ...
,
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 inte ...
, and
stiffness Stiffness is the extent to which an object resists deformation in response to an applied force. The complementary concept is flexibility or pliability: the more flexible an object is, the less stiff it is. Calculations The stiffness, k, of a b ...
. The glass transition temperature of these polymers can exceed 200°C.IUPAC Technical Report (2005)
/ref> COC resins are commonly supplied in pellet form and are suited to standard polymer processing techniques such as single and twin screw
extrusion Extrusion is a process used to create objects of a fixed cross-sectional profile by pushing material through a die of the desired cross-section. Its two main advantages over other manufacturing processes are its ability to create very complex c ...
,
injection molding Injection moulding (U.S. spelling: injection molding) is a manufacturing process for producing parts by injecting molten material into a mould, or mold. Injection moulding can be performed with a host of materials mainly including metals (for ...
, injection
blow molding Blow molding (or moulding) is a manufacturing process for forming hollow plastic parts. It is also used for forming glass bottles or other hollow shapes. In general, there are three main types of blow molding: extrusion blow molding, injection ...
and stretch blow molding (
ISBM Blow molding (or moulding) is a manufacturing process for forming hollow plastic parts. It is also used for forming glass bottles or other hollow shapes. In general, there are three main types of blow molding: extrusion blow molding, injection ...
),
compression molding Compression molding is a method of molding in which the molding material, generally preheated, is first placed in an open, heated mold cavity. The mold is closed with a top force or plug member, pressure is applied to force the material int ...
,
extrusion coating Extrusion coating is the coating of a molten web of synthetic resin onto a substrate material. It is a versatile coating technique used for the economic application of various plastics, notably polyethylene, onto paperboard, corrugated fiberboa ...
, biaxial orientation,
thermoforming Thermoforming is a manufacturing process where a plastic sheet is heated to a pliable forming temperature, formed to a specific shape in a mold, and trimmed to create a usable product. The sheet, or "film" when referring to thinner gauges and cert ...
and many others. COC is noted for high dimensional stability with little change seen after processing. COC and COP are generally attacked by
non-polar In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more pola ...
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s, such as
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...
. COC shows good chemical resistance and barrier to other solvents, such as
alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
, and is very resistant to attack from
acids In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
and bases. Electronic properties of COC are in some respects similar to
fluoropolymers A fluoropolymer is a fluorocarbon-based polymer with multiple carbon–fluorine bonds. It is characterized by a high resistance to solvents, acids, and bases. The best known fluoropolymer is polytetrafluoroethylene under the brand name "Teflon," ...
, most notably a similarly low
dissipation factor In physics, the dissipation factor (DF) is a measure of loss-rate of energy of a mode of oscillation (mechanical, electrical, or electromechanical) in a dissipative system. It is the reciprocal of quality factor, which represents the "quality" or d ...
or tan delta, and low permittivity. It is a very good insulator.


Applications


Packaging

COC is commonly extruded with cast or blown film equipment in the manufacture of packaging films. Most often, due to cost, COC is used as a modifier in monolayer or multilayer film to provide properties not delivered by base resins such as
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 bo ...
. Grades of COC based on ethylene show a certain amount of compatibility with polyethylene and can be blended with PE via commercial dry blending equipment. These films are then used in consumer applications including food and healthcare packaging. Key COC enhancements can include thermoformability, shrink, deadfold, easy tear, enhanced stiffness, heat resistance and higher moisture barrier. Common applications include shrink films and labels, twist films, protective or bubble packaging, and forming films. Another noted application which often relies on a high percentage of COC in the end product is pharmaceutical blister packaging.


Healthcare

The high purity, moisture barrier, clarity, and sterilization compatibility of COC resins make them an excellent alternative to glass in a wide range of medical products. Breakage prevention and weight reduction are common reasons for choosing COC in these applications. COC has a very low-energy and nonreactive
surface A surface, as the term is most generally used, is the outermost or uppermost layer of a physical object or space. It is the portion or region of the object that can first be perceived by an observer using the senses of sight and touch, and is ...
, which can extend shelf life and purity of
medications A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and rel ...
such as insulin and other
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...
drugs in applications such as vials, syringes and cartridges. The high UV transmission of COC also drives diagnostic applications such as
cuvettes A cuvette ( French: cuvette = "little vessel") is a small tube-like container with straight sides and a circular or square cross section. It is sealed at one end, and made of a clear, transparent material such as plastic, glass, or fused quartz. ...
and
microplate A microplate, also known as a microtiter plate (''Microtiter'' is a registered trademark in the United States, therefore it should not be used generically without attribution), microwell plate or multiwell, is a flat plate with multiple "wells" ...
s. COC plays an increasingly important role in
microfluidics Microfluidics refers to the behavior, precise control, and manipulation of fluids that are geometrically constrained to a small scale (typically sub-millimeter) at which surface forces dominate volumetric forces. It is a multidisciplinary field tha ...
due to its chemical resistance, clarity and unusually high mold detail replication which makes it possible to reliably mold submicron features. Most COC grades can undergo sterilization by
gamma radiation A gamma ray, also known as gamma radiation (symbol γ or \gamma), is a penetrating form of electromagnetic radiation arising from the radioactive decay of atomic nuclei. It consists of the shortest wavelength electromagnetic waves, typically s ...
, steam, or
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 a ...
.


Optics

These polymers are commercially used in optical films,
lens A lens is a transmissive optical device which focuses or disperses a light beam by means of refraction. A simple lens consists of a single piece of transparent material, while a compound lens consists of several simple lenses (''elements''), ...
es,
touch screens A touchscreen or touch screen is the assembly of both an input ('touch panel') and output ('display') device. The touch panel is normally layered on the top of an electronic visual display of an information processing system. The display is often ...
, light guide panels, reflection films, and other components for
mobile devices A mobile device (or handheld computer) is a computer small enough to hold and operate in the hand. Mobile devices typically have a flat LCD or OLED screen, a touchscreen interface, and digital or physical buttons. They may also have a physical ...
,
displays A display device is an output device for presentation of information in visual or tactile form (the latter used for example in tactile electronic displays for blind people). When the input information that is supplied has an electrical signal the ...
,
cameras A camera is an optical instrument that can capture an image. Most cameras can capture 2D images, with some more advanced models being able to capture 3D images. At a basic level, most cameras consist of sealed boxes (the camera body), with a ...
,
copiers A photocopier (also called copier or copy machine, and formerly Xerox machine, the generic trademark) is a machine that makes copies of documents and other visual images onto paper or plastic film quickly and cheaply. Most modern photocopiers u ...
and other optical assemblies.


Fiber spinning

COC has unique electrical properties that resist
dielectric In electromagnetism, a dielectric (or dielectric medium) is an electrical insulator that can be polarised by an applied electric field. When a dielectric material is placed in an electric field, electric charges do not flow through the mate ...
breakdown and have a very low dielectric loss over time. Because of this COC is used in filter media that require a charge retention to work properly.Lamonte, Ronald & Donal McNally (June 2000), "Uses and Processing of Cyclic Olefin Copolymers" ''Plastics Engineering''


Electronics

The low dielectric constant of COC, even at high frequency, has led to its use in certain
antenna Antenna ( antennas or antennae) may refer to: Science and engineering * Antenna (radio), also known as an aerial, a transducer designed to transmit or receive electromagnetic (e.g., TV or radio) waves * Antennae Galaxies, the name of two collid ...
applications as well as
capacitors A capacitor is a device that stores electrical energy in an electric field by virtue of accumulating electric charges on two close surfaces insulated from each other. It is a passive electronic component with two terminals. The effect of a ...
requiring higher temperature resistance than
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 propylene. Polypropylene belongs to the group of polyolefins and ...
can provide.


See also

*
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 double bonds). Ethylene i ...
*
Polynorbornene Norbornene or norbornylene or norcamphene is a highly strained bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carr ...


References


External links


Physical and electrical properties of TOPAS
Polymer chemistry Copolymers