Polyethylene naphthalate (PEN)

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Polyethylene naphthalate(PEN)
Moni MurakiHeidi PecoraroCHEM 231November 28,
2005
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Esterification Reaction
ethylene glycerol

H2O
naphthalene dicarboxylic acid
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Ethylenenaphthalene Monomer
naphthalene group
ethylene group
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Condensation Polymerization

• Same reaction that forms monomer
• Step-growth polymerization combines two
  molecules and removes a small molecule
• Polyesters are formed by this mechanism
• Heat (?) catalyzes the reaction
• Not chain-growth polymerization instead any two
  reactive molecules can combine

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PEN Polymerization
H2O
H2O
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PEN Uses

• Can be processed into films, fibers, and
  containers
• Film media tapes
• Fibers electrical insulation, cords/cables, tire
  cord, narrow- and broad-woven fabrics, synthetic
  molecular membranes
• Containers bottles, jars, tableware

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PEN Commercial Products
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PEN A Brief History

• In the UK, ICI Alkali Division laboratories
  produced polyethylene in 1935
• Polyethylene has thermoplastic properties that
  were vital to the development of radar
• 1953 DuPont first commercial production of PEN
  fiber for carpets
• Currently gt2000 patents for PEN products

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PEN Health Risks?

• None found, however
• Exposure to high amounts of naphthalene can
  damage or destroy RBCs and has been shown to
  cause cancer in rats
• Classified as possibly carcinogenic in humans
• Ethylene glycol is a suspected toxin in the
  following systems
• Cardiovascular, developmental, GI, liver, kidney,
  neurological, reproductive, respiratory, and
  skin/sense organs

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PEN Health Risks?

• Polyethylene hazards skin and eye irritation
• Polyethylene terephthalate (PET) a close
  relative of PEN phthalates (which can act as
  endocrine disruptors) leach into water or food if
  the container is heated

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PEN Properties

• High temperature resistance
• High glass transition temp (unlike PET)
• High UV resistance
• Resistant to hydrolysis in alkaline or very hot
  aqueous conditions
• Rigid, transparent, colorless
• Thus, slow degradation

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PEN Recycling

• Commercial recycling firms
• Bottles and jars recyclable and reusable
• Containers can be recycled
• PEN can be sterilized at high temperatures

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References

• E.S. Stevens. 2001. Green Plastics An
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• The History of Plastics. 2005. lthttp//www.bpf.co.
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  November 25, 2005
• Color your carpet. 2005. History of Dyes.
  lthttp//www.coloryourcarpet.com/History/
  DyeHistory.htmlgt, accessed November 25, 2005
• British Petroleum. 2001. Elements naphthalates
  from bp-expanding the use of polyesters.
  1(1)Summer 2001.
• H. Meimberg, S. Thalhammer, A. Brachmann, B.
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• M.S.M. Alger (ed). 1989. Polymer science
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  346p.
• P.Y. Bruice. 2004. Organic Chemistry. 4th ed.
  Pearson Education, Inc. 1148p.
• T. Furatani. 2005. Organic Chemistry Lecture,
  NSCC. November 23, 2005.
• Wikipedia. 2005. Naphthalene. lthttp//en.wikipedia
  .org/wiki/Naphthalenegt, accessed November 18,
  2005.
• Scorecard the pollution information site. 2005.
  Ethylene glycol. lthttp//www. scorecard.org/chemic
  al-profiles/summarygt, accessed November 18, 2005.
• M.L. Berins. 1991. Spi Plastics Engineering
  Handbook of the Society of the Plastics Industry,
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  67p.
• Polymer Science Learning Center. 2005. Polyester.
  lthttp//www.pslc.ws/ mactest/pet.htmgt, accessed
  November 25, 2005.
• Sirex. 2005. 3R-Foam, Range of Applications.
  lthttp//www.recycledfoam. com/applications.htmgt,
  accessed November 25, 2005.
• Landscape Structures. 2005. Recycled Polyethylene
  Bench. lthttp//www.playlsi.com /Products/Accessori
  es/SiteAmenities/RecycledPolytheyleneBench/Recycl
  edPoly Bench.htmgt, accessed November 25, 2005.
• Plastics resource.com. 2005. Information on
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  resource.comgt, accessed November 2, 2005.