Polytetrafluorethylene (PTFE)

Chandra Heller
Michael Mallicote
Discovery
 Accidentally discovered on April 6, 1938
by Roy Plunkett.
Uses
 By 1941, PTFE had been patented and
had its first brand name Teflon®.
 By 1946, the resin product was being
used to produce machine parts for
military and industrial applications.
 In the 1960s it began its life in the arena
of nonstick cookware.
Uses (continued)
 Today it has expanded into a whole
family of polymers (resins, films,
coatings, moldable forms, powders) and
sold under various brand names,
including Gore-Tex® and Zylon®.
 It is used in a wide range of industries
from aerospace to pharmaceuticals and
is sold in over 40 countries worldwide.
Teflon® Monomer

F F
C C

F F

tetrafluoroethylene
Teflon® Polymer
Teflon® Polymer (continued)
 Emulsion Polymerization
Initiation: Free radical formation
ROOR + Heat → 2 RO

Initiation: Formation of new free radicals by peroxide + TFE in aqueous phase

RO + CF2=CF2 → RO(CF2–CF2)

Propagation:
Growth of free radicals by further addition of TFE
RO(CF2–CF2) + n CF2=CF2 → RO(CF2–CF2)–(CF2–CF2)

Free radicals undergo hydrolysis where a hydroxyl group replaces the peroxide
RO(CF2–CF2)–(CF2–CF2) + H2O → HO(CF2–CF2)n–(CF2–CF2) + H+ + HOR

HO(CF2=CF2)n–(CF2=CF2) + H2O → COOHCF2–(CF2–CF2) n + 2HF

Termination:
COOH– CF2–(CF2– CF2) n + COOH– CF2–(CF2– CF2) m → COOH– CF2–(CF2– CF2) m+n
COOH
Toxicity
 The monomer TFE is a confirmed animal
carcinogen with unknown relevance to
humans.
 The finished polymer in solid form is inert
under ordinary conditions. There is some
indication that the powdered forms of PTFE
may be carcinogenic if inhaled.
Recycling of PTFE
 It is easy to recycle since no chemical
reaction is necessary.
 Only the extruded forms are recycled (not the
resin or powerdered forms).
 The uses of recycled PTFE are restricted.
 It is typically ground up into fine powders and
used as additives in such products as inks,
paints, and cosmetics.
Questions
References
1) Inventor of the Week: Archive. http://web.mit.edu/invent/iow/plunkett.html (2000)
2) Teflon.com - the complete resource on Teflon® products by DuPont.
http://www.teflon.com/NASApp/Teflon/TeflonPageServlet?pageId=/consumer/na/home_page.jsp (2005)
3) Biomaterials. http://www.abe.msstate.edu/Classes/abe4523_6523/polymers.PDF (2001)
4) Zonyl Packaging: Whistleblower. http://www.mindfully.org/Plastic/Teflon/Zonyl-DuPont-Risk17nov05.htm (2005)
5) Teflon fluorocarbon information. http://www.omega.com/techref/fluoro.html (2001)
6) Polymers. http://www.chemistry.mtu.edu/pages/courses/ch1120-pcharles/Oxtoby_Ch25.pdf (2004)
7) Ebnesajjad, S. Non-melt Processible Fluoroplastics : The Definitive User's Guide and Databook. Norwich, N.Y. :
Plastics Design Library. (2000)
8) Ebnesajjad, S. Melt Processible Fluoropolymers: The Definitive User's Guide and Databook. Norwich, N.Y. : Plastics
Design Library (2003)
9) Chemical Structure. http://www.eng.utah.edu/~nairn/mse/students/MSE3410/Teflon/Chemical_Structure.html (2003)
10) Synthesis. http://www.eng.utah.edu/~nairn/mse/students/MSE3410/Teflon/synthesis.html. (2003)
11) Burridge, E. PTFE. Eur. Chem. News. 80, 16 (2004)
12) Bingham, E., Cohrssen, B., Powell, C., Eds. Patty's Toxicology. New York : John Wiley. (2001)
13) Useless Information. http://home.nycap.rr.com/useless/teflon/ (2003)
14) DuPont Electronic Materials Keep Mars Rovers Going.
http://www2.dupont.com/Teflon_Industrial/en_US/news_events/article20050120.html (2005)
15) National Toxicology Program. http://ntp.niehs.nih.gov/ (2005)
16) Learn more about Teflon®.
http://www.teflon.com/NASApp/Teflon/TeflonPageServlet?pageId=/consumer/na/eng/housewares/keyword/teflon_ke
yword_birds.html (2005)
17) NIOSH: The National Institute for Occupational Safety and Health. http://www.cdc.gov/niosh/homepage.html (2005)
18) Recycling. http://www.eng.utah.edu/~nairn/mse/students/MSE3410/Teflon/Recycling.html (2003)