Polychlorotrifluoroethylene

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Polychlorotrifluoroethylene
Polychlorotrifluoroethylene.svg
Names
Other names
Poly(1-chloro-1,2,2-trifluoroethylene)
Poly(ethylene trifluoride chloride)
Polymonochlorotrifluoroethylene
Poly(trifluoroethylene chloride)
Poly(chlorotrifluoroethylene)
Poly(trifluorochloroethene)
Poly(chlorotrifluoroethene)
Poly(trifluorovinyl chloride)
Poly(vinyl trifluorochloride)
Kel-F 300; Kel-F 81
Identifiers
AbbreviationsPCTFE, PTFCE [1]
ChemSpider
  • None
ECHA InfoCard 100.120.473 OOjs UI icon edit-ltr-progressive.svg
MeSH Polychlorotrifluoroethene
Properties
(C2ClF3)n°°
Molar mass Variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [2]

Contents

History

It was discovered in 1934 [3] [4] by Fritz Schloffer and Otto Scherer who worked at IG Farben Company, Germany. [5]

Trade names

After World War II, PCTFE was commercialized under the trade name of Kel-F 81 by M. W. Kellogg Company in early 1950s. [6] The name "Kel-F" was derived from "Kellogg" and "fluoropolymer", which also represents other fluoropolymers like the copolymer poly(chlorotrifluoroethylene-co-vinylidene fluoride) (Kel-F 800). [7] These were acquired by 3M Company in 1957. [6] But 3M discontinued manufacturing of Kel-F by 1996.

PCTFE resin is now manufactured in different trade names such as Neoflon PCTFE from Daikin, Voltalef from Arkema or Aclon from Allied Signal. PCTFE films are sold under the tradename Aclar by Allied Signal. [8] Tradenames of PCTFE in other manufacturing companies include Hostaflon C2 from Hoechst, Fluon from ICI, Aclar from Honeywell, Plaskon from Allied Chemical Corporation, Halon from Ausimont USA, [9] [10] and Ftoroplast-3 in USSR and Russian Federation. [11]

Synthesis

PCTFE is an addition homopolymer. It is prepared by the free-radical polymerization of chlorotrifluoroethylene (CTFE) [12] and can be carried out by solution, bulk, suspension and emulsion polymerization. [13]

Properties

PCTFE has high tensile strength and good thermal characteristics. It is nonflammable [14] and the heat resistance is up to 175 °C. [15] It has a low coefficient of thermal expansion. The glass transition temperature (Tg) is around 45 °C. [1]

PCTFE has one of the highest limiting oxygen index (LOI). [16] It has good chemical resistance. It also exhibits properties like zero moisture absorption and non wetting. [15] [17]

It does not absorb visible light. When subjected to high-energy radiation, it undergoes degradation like PTFE. [18] It can be used as a transparent film. [14]

The presence of a chlorine atom, having greater atomic radius than that of fluorine, hinders the close packing possible in PTFE. This results in having a relatively lower melting point among fluoropolymers, [19] around 210–215 °C. [2]

PCTFE is resistant to the attack by most chemicals and oxidizing agents, a property exhibited due to the presence of high fluorine content. However, it swells slightly in halocarbon compounds, ethers, esters and aromatic compounds. [2] PCTFE is resistant to oxidation because it does not have any hydrogen atoms. [20]

PCTFE exhibits a permanent dipole moment due to the asymmetry of its repeating unit. This dipole moment is perpendicular to the carbon-chain axis. [21]

Differences from PTFE

PCTFE is a homopolymer of chlorotrifluoroethylene (CTFE), whereas PTFE is a homopolymer of tetrafluoroethylene. The monomers of the former differs from that of latter structurally by having a chlorine atom replacing one of the fluorine atoms. Hence each repeating unit of PCTFE have a chlorine atom in place of a fluorine atom. This accounts for PCTFE to have less flexibility of chain and hence higher glass transition temperature. PTFE has a higher melting point and is more crystalline than PCTFE, but the latter is stronger and stiffer. Though PCTFE has excellent chemical resistance, it is still less than that of PTFE. [22] PCTFE has lower viscosity, higher tensile strength and creep resistance than PTFE. [1]

PCTFE is injection-moldable and extrudable, whereas PTFE is not. [1]

Applications

PCTFE finds majority of its application due to two main properties: water repulsion and chemical stability. PCTFE films are used as a protective layer against moisture. These include:

Due to its chemical stability, it acts as a protective barrier against chemicals. It is used as a coating and prefabricated liner for chemical applications. PCTFE is also used for laminating other polymers like PVC, polypropylene, PETG, APET etc. It is also used in transparent eyeglasses, tubes, valves, chemical tank liners, O-rings, seals and gaskets. [15]

PCTFE is used to protect sensitive electronic components because of its excellent electrical resistance and water repulsion. Other uses include flexible printed circuits and insulation of wires and cables. [24] [22]

Low-molecular-weight PCTFE waxes, oils and greases find their application as inert sealants and lubricants. They are also used as gyroscope flotation fluids and plasticizers for thermoplastics. [2]

The cryogenic and liquid gas sector uses mainly PCTFE seals for their sealing solution as this material has low gas absorption and resist to temperature below 200 °C.

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">Polytetrafluoroethylene</span> Synthetic polymer

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 DuPont, which originally discovered the compound in 1938.

<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">Polyvinylidene fluoride</span> Non-reactive thermoplastic fluoropolymer

Polyvinylidene fluoride or polyvinylidene difluoride (PVDF) is a highly non-reactive thermoplastic fluoropolymer produced by the polymerization of vinylidene difluoride. Its chemical formula is (C2H2F2)n.

<span class="mw-page-title-main">Copolymer</span> Polymer derived from more than one species of monomer

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 sometimes called bipolymers. Those obtained from three and four monomers are called terpolymers and quaterpolymers, respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material.

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," trademarked by the DuPont Company.

<span class="mw-page-title-main">Polyoxymethylene</span> Engineering thermoplastic polymer

Polyoxymethylene (POM), also known as acetal, polyacetal, and polyformaldehyde, is an engineering thermoplastic used in precision parts requiring high stiffness, low friction, and excellent dimensional stability. As with many other synthetic polymers, it is produced by different chemical firms with slightly different formulas and sold variously by such names as Delrin, Kocetal, Ultraform, Celcon, Ramtal, Duracon, Kepital, Polypenco, Tenac and Hostaform.

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

Polyvinyl fluoride (PVF) or –(CH2CHF)n– is a polymer material mainly used in the flammability-lowering coatings of airplane interiors and photovoltaic module backsheets. It is also used in raincoats and metal sheeting. Polyvinyl fluoride is a thermoplastic fluoropolymer with a repeating vinyl fluoride unit, and it is structurally very similar to polyvinyl chloride.

<span class="mw-page-title-main">ECTFE</span> Corrosion-resistant polymer

ECTFE (ethylene-chlorotrifluoroethylene) is an alternating copolymer of ethylene and chlorotrifluoroethylene. It is a semi-crystalline fluoropolymer, with chemical corrosion resistance properties.

Chlorotrifluoroethylene (CTFE) is a chlorofluorocarbon with chemical formula CFCl=CF2. It is commonly used as a refrigerant in cryogenic applications. CTFE has a carbon-carbon double bond and so can be polymerized to form polychlorotrifluoroethylene or copolymerized to produce the plastic ECTFE. PCTFE has the trade name Neoflon PCTFE from Daikin Industries in Japan, and it used to be produced under the trade name Kel-F from 3M Corporation in Minnesota.

<span class="mw-page-title-main">Cyclic olefin copolymer</span> Chemical compound

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.

Perfluoroethers are a class of organofluorine compound containing one or more ether functional group. In general these compounds are structurally analogous to the related hydrocarbon ethers, except for the distinctive properties of fluorocarbons.

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

A perfluorinated compound (PFC) or perfluoro compound is an organofluorine compound that lacks C-H bonds. Many perfluorinated compounds have properties that are quite different from their C-H containing analogues. Common functional groups in PFCs are OH, CO2H, chlorine, O, and SO3H. Electrofluorination is the predominant method for PFC production. Due to their chemical stability, some of these perfluorinated compounds bioaccumulate.

Polyaryletherketone (PAEK) is a family of semi-crystalline thermoplastics with high-temperature stability and high mechanical strength whose molecular backbone contains alternately ketone (R-CO-R) and ether groups (R-O-R). The linking group R between the functional groups consists of a 1,4-substituted aryl group.

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

Poly(3-hydroxybutyrate-co-3-hydroxyvalerate), commonly known as PHBV, is a polyhydroxyalkanoate-type polymer. It is biodegradable, nontoxic, biocompatible plastic produced naturally by bacteria and a good alternative for many non-biodegradable synthetic polymers. It is a thermoplastic linear aliphatic polyester. It is obtained by the copolymerization of 3-hydroxybutanoic acid and 3-hydroxypentanoic acid. PHBV is used in speciality packaging, orthopedic devices and in controlled release of drugs. PHBV undergoes bacterial degradation in the environment.

Fluorine forms a great variety of chemical compounds, within which it always adopts an oxidation state of −1. With other atoms, fluorine forms either polar covalent bonds or ionic bonds. Most frequently, covalent bonds involving fluorine atoms are single bonds, although at least two examples of a higher order bond exist. Fluoride may act as a bridging ligand between two metals in some complex molecules. Molecules containing fluorine may also exhibit hydrogen bonding. Fluorine's chemistry includes inorganic compounds formed with hydrogen, metals, nonmetals, and even noble gases; as well as a diverse set of organic compounds. For many elements the highest known oxidation state can be achieved in a fluoride. For some elements this is achieved exclusively in a fluoride, for others exclusively in an oxide; and for still others the highest oxidation states of oxides and fluorides are always equal.

<span class="mw-page-title-main">Fluorochemical industry</span> Industry dealing with chemicals from fluorine

The global market for chemicals from fluorine was about US$16 billion per year as of 2006. The industry was predicted to reach 2.6 million metric tons per year by 2015. The largest market is the United States. Western Europe is the second largest. Asia Pacific is the fastest growing region of production. China in particular has experienced significant growth as a fluorochemical market and is becoming a producer of them as well. Fluorite mining was estimated in 2003 to be a $550 million industry, extracting 4.5 million tons per year.

<span class="mw-page-title-main">Perfluoroalkoxy alkane</span> Family of polymers

Perfluoroalkoxy alkanes (PFA) are fluoropolymers. They are copolymers of tetrafluoroethylene (C2F4) and perfluoroethers (C2F3ORf, where Rf is a perfluorinated group such as trifluoromethyl (CF3)). The properties of these polymers are similar to those of polytetrafluoroethylene (PTFE). Compared to PTFE, PFA has better anti-stick properties and higher chemical resistance, at the expense of lesser scratch resistance.

<span class="mw-page-title-main">High-performance plastics</span> Plastics that meet higher requirements than engineering plastics

High-performance plastics are plastics that meet higher requirements than standard or engineering plastics. They are more expensive and used in smaller amounts.

Polytetrafluoroethylene (PTFE), better known by its trade name Teflon, has many desirable properties which make it an attractive material for numerous industries. It has good chemical resistance, a low dielectric constant, low dielectric loss, and a low coefficient of friction, making it ideal for reactor linings, circuit boards, and kitchen utensils, to name a few applications. However, its nonstick properties make it challenging to bond to other materials or to itself.

References

  1. 1 2 3 4 Christopher C. Ibeh (2011). THERMOPLASTIC MATERIALS Properties, Manufacturing Methods, and Applications. CRC Press. p. 491. ISBN   978-1-4200-9383-4.
  2. 1 2 3 4 C. H. Kurita (20 Jan 1988). "Appendix A" (PDF). D-ZERO COLD VALUE. pp. 58–61. Archived from the original (PDF) on 21 October 2013. Retrieved June 14, 2012.
  3. ↑ Tsuyoshi Nakajima; Henri Groult (4 August 2005). Fluorinated Materials For Energy Conversion. Elsevier. p. 472. ISBN   978-0-08-044472-7 . Retrieved 14 July 2012.
  4. ↑ B. Améduri; Bernard Boutevin (7 July 2004). Well-architectured Fluoropolymers: Synthesis, Properties And Applications. Elsevier. p. 5. ISBN   978-0-08-044388-1 . Retrieved 14 July 2012.
  5. ↑ Koch 2012, p. 11.
  6. 1 2 Takashi Okazoe. "Synthetic Studies on Perfluorinated Compounds by Direct Fluorination" (PDF). p. 17. Retrieved July 14, 2012.
  7. ↑ Suhithi M. Peiris; Gasper J. Piermarini (10 December 2008). Static Compression of Energetic Materials. Springer. pp. 158–. ISBN   978-3-540-68146-5 . Retrieved 14 July 2012.
  8. ↑ Sina Ebnesajjad (31 December 2000). Fluoroplastics, Volume 1: Non-Melt Processible Fluoroplastics. William Andrew. p. 74. ISBN   978-0-8155-1727-6 . Retrieved 8 July 2012.
  9. ↑ DIANE Publishing Company (1 July 1993). New Materials Society, Challenges and Opportunities: New Materials Science and Technology. DIANE Publishing. p. 8.42. ISBN   978-0-7881-0147-2 . Retrieved 8 July 2012.
  10. ↑ Ernst-Christian Koch (17 April 2012). Metal-Fluorocarbon Based Energetic Materials. John Wiley & Sons. p. 23. ISBN   978-3-527-32920-5 . Retrieved 8 July 2012.
  11. ↑ ГОСТ 13744-83 State Standard of USSR
  12. ↑ Sina Ebnesajjad (31 December 2002). Melt Processible Fluoropolymers: The Definitive User's Guide and Databook. William Andrew. p. 636. ISBN   978-1-884207-96-9 . Retrieved 8 July 2012.
  13. ↑ Ebnesajjad 2000, p. 61.
  14. 1 2 Ruth Winter (2 August 2007). A Consumer's Dictionary of Household, Yard and Office Chemicals: Complete Information About Harmful and Desirable Chemicals Found in Everyday Home Products, Yard Poisons, and Office Polluters. iUniverse. p. 255. ISBN   978-0-595-44948-4 . Retrieved 14 July 2012.
  15. 1 2 3 François Cardarelli (2008). Materials Handbook: A Concise Desktop Reference. Springer. pp. 708–709. ISBN   9781846286681. ISBN   1846286689.
  16. ↑ Ebnesajjad, Sina. Fluoroplastics, Volume 2: Melt Processible Fluoropolymers – The Definitive User Guide and Data Book. p. 560.
  17. ↑ "RIDOUT PLASTICS" . Retrieved June 5, 2012.
  18. ↑ J. A. Brydson (8 November 1999). Plastics Materials. Butterworth-Heinemann. pp. 423–. ISBN   978-0-7506-4132-6 . Retrieved 30 June 2012.
  19. ↑ Drobny 2006, p. 8, 22.
  20. ↑ "Chapter Two: Sixth Part". Archived from the original on 2012-01-07. Retrieved 2012-06-13.
  21. ↑ "Dielectric Properties of Semicrystalline Polychlorotrifluoroethylene" (PDF). Journal of Research of the National Bureau of Standards Section A. 66A (4): 1. 1962. Retrieved June 26, 2012.
  22. 1 2 Dominick V. Rosato; Donald V. Rosato; Matthew V. Rosato (2004). Plastic Product Material and Process Selection Handbook. Elsevier. p. 75. ISBN   185617431X. ISBN   9781856174312.
  23. ↑ "Technical plastics for cryogenics". Société des Plastiques Nobles. Retrieved 2020-02-14.
  24. ↑ Drobny 2006, p. 37-39.
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