Cyclic olefin copolymer

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Cyclic olefin copolymer
Cyclic Olefin Copolymer.png
Names
Other names
COC, cyclic olefin polymer, cyclo olefin copolymer, ethylene-norbornene copolymer
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C7H10.C2H4/c1-2-7-4-3-6(1)5-7;1-2/h1-2,6-7H,3-5H2;1-2H2 Yes check.svgY
    Key: SFFFIHNOEGSAIH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H10.C2H4/c1-2-7-4-3-6(1)5-7;1-2/h1-2,6-7H,3-5H2;1-2H2
    Key: SFFFIHNOEGSAIH-UHFFFAOYAJ
  • C=C.C\1=C\C2CC/1CC2
Properties
AppearanceClear resin
Density 1.02 g/cm3, solid
Hazards
Safety data sheet (SDS) COC US MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 and polyethylene. This newer material is used in a wide variety of applications including packaging films, lenses, vials, displays, and medical devices.

Contents

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) or 1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene (tetracyclododecene) with ethene (such as Polyplastics subsidiary TOPAS Advanced Polymers' TOPAS, Mitsui Chemical's APEL), or by ring-opening metathesis polymerization of various cyclic monomers followed by hydrogenation (Japan Synthetic Rubber's ARTON, Zeon Chemical's Zeonex and Zeonor)." [1] 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 and PP, similar to PET 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-free and BPA-free product. Some grades of COC have shown a lack of estrogenic activity. [2]

The optical properties of COC are exceptional, and in many ways very similar to glass. COC materials offer exceptional transparency, low birefringence, high Abbe number 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, viscosity, and stiffness. The glass transition temperature of these polymers can exceed 200°C. [1] COC resins are commonly supplied in pellet form and are suited to standard polymer processing techniques such as single and twin screw extrusion, injection molding, injection blow molding and stretch blow molding (ISBM), compression molding, extrusion coating, biaxial orientation, thermoforming 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 solvents, such as toluene. COC shows good chemical resistance and barrier to other solvents, such as alcohols, and is very resistant to attack from acids and bases.

Electronic properties of COC are in some respects similar to fluoropolymers, most notably a similarly low dissipation factor or tan delta, and low permittivity. It is a very good insulator. [3]

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. 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. [4]

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, which can extend shelf life and purity of medications such as insulin and other protein drugs in applications such as vials, syringes and cartridges. The high UV transmission of COC also drives diagnostic applications such as cuvettes and microplates. COC plays an increasingly important role in microfluidics due to its chemical resistance, clarity and unusually high mold detail replication which makes it possible to reliably mold submicron features. [5] Most COC grades can undergo sterilization by gamma radiation, steam, or ethylene oxide.

Optics

These polymers are commercially used in optical films, lenses, touch screens, light guide panels, reflection films, and other components for mobile devices, displays, cameras, copiers and other optical assemblies.

Fiber spinning

COC has unique electrical properties that resist dielectric 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. [6]

Electronics

The low dielectric constant of COC, even at high frequency, has led to its use in certain antenna applications as well as capacitors requiring higher temperature resistance than polypropylene can provide.

See also

Related Research Articles

<span class="mw-page-title-main">Polymer</span> Substance composed of macromolecules with repeating structural units

A polymer (;) is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic and natural polymers play essential and ubiquitous roles in everyday life. Polymers range from familiar synthetic plastics such as polystyrene to natural biopolymers such as DNA and proteins that are fundamental to biological structure and function. Polymers, both natural and synthetic, are created via polymerization of many small molecules, known as monomers. Their consequently large molecular mass, relative to small molecule compounds, produces unique physical properties including toughness, high elasticity, viscoelasticity, and a tendency to form amorphous and semicrystalline structures rather than crystals.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Polyethylene</span> Most common thermoplastic polymer

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 bottles, etc.). As of 2017, over 100 million tonnes of polyethylene resins are being produced annually, accounting for 34% of the total plastics market.

<span class="mw-page-title-main">Thermoplastic</span> Plastic that softens with heat and hardens on cooling

A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling.

<span class="mw-page-title-main">Polyethylene terephthalate</span> Polymer

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 foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening ("curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure or mixing with a catalyst. Heat is not necessarily applied externally, and is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

<span class="mw-page-title-main">Polychlorotrifluoroethylene</span> Chemical compound

Polychlorotrifluoroethylene (PCTFE or PTFCE) is a thermoplastic chlorofluoropolymer with the molecular formula (CF2CClF)n, where n is the number of monomer units in the polymer molecule. It is similar to polytetrafluoroethene (PTFE), except that it is a homopolymer of the monomer chlorotrifluoroethylene (CTFE) instead of tetrafluoroethene. It has the lowest water vapor transmission rate of any plastic.

<span class="mw-page-title-main">High-density polyethylene</span> Class of polyethylenes

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, HDPE is used in the production of plastic bottles, corrosion-resistant piping, geomembranes and plastic lumber. HDPE is commonly recycled, and has the number "2" as its resin identification code.

<span class="mw-page-title-main">Polyethylene naphthalate</span> Chemical compound

Polyethylene naphthalate is a polyester derived from naphthalene-2,6-dicarboxylic acid and ethylene glycol. As such it is related to poly(ethylene terephthalate), but with superior barrier properties.

A polyolefin is a type of polymer with the general formula (CH2CHR)n where R is an alkyl group. They are usually derived from a small set of simple olefins (alkenes). Dominant in a commercial sense are polyethylene and polypropylene. More specialized polyolefins include polyisobutylene and polymethylpentene. They are all colorless or white oils or solids. Many copolymers are known, such as polybutene, which derives from a mixture of different butene isomers. The name of each polyolefin indicates the olefin from which it is prepared; for example, polyethylene is derived from ethylene, and polymethylpentene is derived from 4-methyl-1-pentene. Polyolefins are not olefins themselves because the double bond of each olefin monomer is opened in order to form the polymer. Monomers having more than one double bond such as butadiene and isoprene yield polymers that contain double bonds (polybutadiene and polyisoprene) and are usually not considered polyolefins. Polyolefins are the foundations of many chemical industries.

<span class="mw-page-title-main">Hot-melt adhesive</span> Glue applied by heating

Hot-melt adhesive (HMA), also known as hot glue, is a form of thermoplastic adhesive that is commonly sold as solid cylindrical sticks of various diameters designed to be applied using a hot glue gun. The gun uses a continuous-duty heating element to melt the plastic glue, which the user pushes through the gun either with a mechanical trigger mechanism on the gun, or with direct finger pressure. The glue squeezed out of the heated nozzle is initially hot enough to burn and even blister skin. The glue is sticky when hot, and solidifies in a few seconds to one minute. Hot-melt adhesives can also be applied by dipping or spraying, and are popular with hobbyists and crafters both for affixing and as an inexpensive alternative to resin casting.

<span class="mw-page-title-main">Fluorinated ethylene propylene</span> Polymer

Fluorinated ethylene propylene (FEP) is a copolymer of hexafluoropropylene and tetrafluoroethylene. It differs from the polytetrafluoroethylene (PTFE) resins in that it is melt-processable using conventional injection molding and screw extrusion techniques. Fluorinated ethylene propylene was invented by DuPont and is sold under the brandname Teflon FEP. Other brandnames are Neoflon FEP from Daikin or Dyneon FEP from Dyneon/3M.

<span class="mw-page-title-main">Blister pack</span> Type of packaging

A blister pack is any of several types of pre-formed plastic packaging used for small consumer goods, foods, and for pharmaceuticals.

<span class="mw-page-title-main">Parylene</span> Chemical compound

Parylene is the common name of a polymer whose backbone consists of para-benzenediyl rings –C
6
H
4
– connected by 1,2-ethanediyl bridges –CH
2
CH
2
–. It can be obtained by polymerization of para-xylyleneH
2
C
=C
6
H
4
=CH
2
.

<span class="mw-page-title-main">Polybenzoxazine</span> Type of bicyclic heterocyclic monomer

Polybenzoxazines, also called benzoxazine resins, are cured polymerization products derived from benzoxazine monomers.

<span class="mw-page-title-main">Polymethylpentene</span> Chemical compound

Polymethylpentene (PMP), also known as poly(4-methyl-1-pentene), is a thermoplastic polyolefin. It is used for gas-permeable packaging, autoclavable medical and laboratory equipment, microwave components, and cookware. It is commonly called TPX, which is a trademark of Mitsui Chemicals.

<span class="mw-page-title-main">Plastic bottle</span> Narrow-necked container

Consumer blow molded containers often have integral handles or are shaped to facilitate grasping.

<span class="mw-page-title-main">Twinwall plastic</span>

Twin-wall plastic, specifically twin-wall polycarbonate, is an extruded multi-wall polymer product created for applications where its strength, thermally insulative properties, and moderate cost are ideal. Polycarbonate, which is most commonly formed through the reaction of Bisphenol A and Carbonyl Chloride, is an extremely versatile material. It is significantly lighter than glass, while managing to be stronger, more flexible, and more impact resistant. Twin-wall polycarbonate is used most commonly for green houses, where it can support itself in a structurally sound configuration, limit the amount of UV light due to its nominal translucence, and can withstand the rigors of daily abuse in an outdoor environment. The stagnant air in the cellular space between sheets provides insulation, and additional cell layers can be extruded to enhance insulative properties at the cost of light transmission.

<span class="mw-page-title-main">Cyclohexanedimethanol</span> Chemical compound

Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.

<span class="mw-page-title-main">Graft polymer</span> Polymer with a backbone of one composite and random branches of another composite

In polymer chemistry, graft polymers are segmented copolymers with a linear backbone of one composite and randomly distributed branches of another composite. The picture labeled "graft polymer" shows how grafted chains of species B are covalently bonded to polymer species A. Although the side chains are structurally distinct from the main chain, the individual grafted chains may be homopolymers or copolymers. Graft polymers have been synthesized for many decades and are especially used as impact resistant materials, thermoplastic elastomers, compatibilizers, or emulsifiers for the preparation of stable blends or alloys. One of the better-known examples of a graft polymer is a component used in high impact polystyrene, consisting of a polystyrene backbone with polybutadiene grafted chains.

References

  1. 1 2 IUPAC Technical Report (2005)
  2. Yang, C. Z.; Yaniger, S. I.; Jordan, V. C.; Klein, D. J.; Bittner, G. D. (2011). "Yang et al (July 2011), "Most Plastic Products Release Estrogenic Chemicals: A Potential Health Problem That Can Be Solved" Environmental Health Perspectives". Environmental Health Perspectives. 119 (7): 989–996. doi:10.1289/ehp.1003220. PMC   3222987 . PMID   21367689. S2CID   18809650.
  3. Tanisho et al., US Patent 6630234 (2003)
  4. "Beer, Ekkehard, Drost, Stephen, Frayer, Becky & Kurt Trombley (June 2004), "The Benefits of Cyclic Olefin Copolymer" Pharmaceutical and Medical Packaging News". Archived from the original on 2007-09-28. Retrieved 2007-07-16.
  5. Mateusz L. Hupert, Joshua M. Jackson, Hong Wang, Małgorzata A. Witek, Joyce Kamande, Matthew I. Milowsky, Young E. Whang, Steven A. Soper, "Arrays of high-aspect ratio microchannels for high-throughput isolation of circulating tumor cells (CTCs)" 2014, Microsystem Technologies, 20(10), pp. 1815-1825
  6. Lamonte, Ronald & Donal McNally (June 2000), "Uses and Processing of Cyclic Olefin Copolymers" Plastics Engineering