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Name Chemical unit Uses Name Chemical unit Uses

H CH 3
Polyvinyl acetate Mixed with vinyl
H H C C chloride to make
Polyethylene Squeeze bottles, vinylite; used as an
containers, H O
C C adhesive and resin
laundry and trash bags, in paint
H H packaging C CH 3
n O
n
Polypropylene H H Indoor-outdoor carpet, Styrene-butadiene H H H H H H Automobile tires
pipe valves, bottles rubber
C C C C C C C C
H CH 3 H H H
n n

Polyvinyl chloride H H Plumbing pipes, synthetic Polychloroprene H Cl H H Shoe soles, heels
(PVC) leather, plastic tablecloths, (Neoprene)
C C C C C C
phonograph records,
vinyl tile
H Cl H H
n n
H Cl
Polyvinylidene Flexible food wrap Polymethyl H CH 3 Moldings, transparent
chloride (Saran)
C C methacrylate C C surfaces on furniture,
(Plexiglas, Lucite) lenses, jewelry,
H Cl H transparent plastic
n n “glass”
C O CH 3
Polystyrene H H Coolers, cups,
(Styrofoam) insulating foam, shock- O
C C
resistant packing material,
simulated wood furniture
H Polycarbonate CH 3 Tough, molded
n (Lexan) articles such as
C O C O
motorcycle helmets
CH 3 O
Polytetrafluoroethylene F F Gears, bearings, coating n
(Teflon) for nonstick surface of
C C
cooking utensils
F F Polyacrylonitrile H H Textile fibers
n (Orlon, Acrilan, C C
Creslan)
H CN
n
FIGURE 12.24 Synthetic polymers, the polymer unit, and some uses of each polymer.

of nitric and sulfuric acids, which produced an ester of cellulose polymer is forced through a thin slit, a sheet is formed rather
nitrate. This ester is an explosive compound known as “gun- than filaments, and the transparent sheet is called cellophane.
cotton,” or smokeless gunpowder. When made with ethanol Both rayon and cellophane, like celluloid, are manufactured by
and camphor, the product is less explosive and can be formed modifying the natural polymer of cellulose.
and molded into useful articles. This first plastic, celluloid, was The first truly synthetic polymer was produced in the early
used to make dentures, combs, eyeglass frames, and photo- 1900s by reacting two chemicals with relatively small molecules
graphic film. Before the discovery of celluloid, many of these rather than modifying a natural polymer. Phenol, an aromatic
articles, including dentures, were made from wood. Today, only hydrocarbon, was reacted with formaldehyde, the simplest alde-
Ping-Pong balls are made from cellulose nitrate. hyde, to produce the polymer named Bakelite. Bakelite is a thermo-
Cotton or other sources of cellulose reacted with acetic acid setting material that forms cross-links between the polymer chains.
and sulfuric acid produce a cellulose acetate ester. This poly- Once the links are formed during production, the plastic becomes
mer, through a series of chemical reactions, produces viscose permanently hardened and cannot be softened or made to flow.
rayon filaments when forced through small holes. The filaments Some plastics are thermoplastic polymers and soften during heating
are twisted together to form viscose rayon thread. When the and harden during cooling because they do not have cross-links.

12-17 CHAPTER 12 Organic Chemistry 315