Chapter 19: Plastics, Water, and Rubbing
Alcohol
Production of selected plastics and related
materials in United States, 1990
Low-density polyethylene = 5.5 million
Poly(vinyl chloride) and copolymers= 4.2m
High-density polyethylene =4m
Polypropylene =4m
Polystyrene = 2.5m
Poly(ethylene terephthalate) and other
polysesters = 1.5m
Phenol-formaldehyde resins = 1.5m
Nylon = 1.4m
Styrex butadiene rubber = 1m
Major Applications
Packaging - 29%
Construction - 21%
Other - 12%
Exports - 8%
Consumer products - 8%
Electrical and electronics - 6%
Adhesive, inks and coatings - 5%
Furniture and furnishings - 5%
Transportation - 5%
Industrial - 1%
Plastic - a material capable of being shaped
into virtually any form
-Greek word “plastikos” - suitable for molding or
shaping
-refers mostly to a property of material
Polymers - a molecule of very high molecular
weight formed by the repeated chemical linking
of a great many simpler, smaller molecules
-Greek words “poly” many and “meros” parts
-extremely large molecules, also referred as
macromolecules
Monomers - individual structures linked to each
other to form a polymer
-Greek word “mono” one
Homopolymers - polymers whose monomers
are mutually identical
- starch and cellulose is an example; gluclose-
monomeric unit
-subscript n = represents a very large but
unspecified number of links
-short, horizontal lines = represents the covalent
bonds linking X to its neighbors
Cellulose - chemical formula: C6H10O5
Copolymers - polymers consisting of chains
composed of two or more different kinds of links
-protein chains; amino acids- monomeric unit
-nylon- another example
Protein- chemical formula: RCH(NH2)COOH,
Polymerization - process whereby individual
monomers link together to form a polymer
Two broad categories: condensation
polymerization and addition polymerization
Products: condensation polymers and addition
polymers
Condensation polymerization -
polysaccharides and protein; good examples
-in condensation reaction, two molecules
combine with the formation and the loss of
another
-droplets of condensate collect on the sides of
the flask
-condensation reaction generates vapors of
compounds being eliminated
Addition polymerization - polymers form as
their individual, unconnected monomers join
together to form a polymeric chain
-in a rough analogy, each pair of hands
corresponds to a pair of bonding electrons
Wallace H. Carothers - an Iowa-born chemist,
left his post as an instructor in organic chemistry
at Harvard University to lead a research group
-found that polymerizing a mixture of adipic acid
and 1,6-diaminohexane could produce nylon
Adipic acid - Latin word “a fat”, formed by
oxidizing fats with nitric acid
Nylon - linear polymer, a condensation polymer
-adipic acid and 1,6-diaminohexane =
monomeric units
-nylon 6,6 = produced from 6 adipic acid and six
carbon 1,6 diamimohexane
-nylon 6 = forms as the ring of caprolactam
opens
Polyethylene - an addition polymer
Thermoplastics - plastics that soften when
heated, then harden again as they cool
-mimic fats in their response to heat
-more popular than thermosets
-e.g. nylon and polyethylene
Thermosets - or thermosetting plastics, plastics
that hold their shape, even when they are
heated
-mimic eggs in their irreversible changes from
heating
-e.g. bakelite and epoxy resins
Bakelite - a strong material and a poor
conductor of heat and electricity
-used in making handles for cooking and
utensils
-used in molding parts for electrical goods
e.g. buttons and billiard balls
Epoxy resins - making fiberboard and plywood
Leather, fabrics of wool, silk - proteins
Cotton - a polysaccharide
Christopher Columbus - found the inhabitants
of the newly discovered Western Hemisphere
playing with rubber
Rubbers - belong to the class of polymers
called elastomers, substances that stretch easily
and return readily to their original shapes
- 2- methyl-1,3-butadiene
-chemical name: isoprene, chemical formula:
C5H8
Gutta-percha - in trans-configuration of
geometry, and isn’t nearly as elastic as rubber
-used for covering of golf balls, surgical
equipment, electrical insulator
Charles Goodyear - born in 1800 in New
Haven, Connecticut, four days after Christmas,
solved the problem of sticky rubber by accident
(serendipity)
-accidentally dropped a natural rubber and sulfur
on a hot stove
-discovered the process that became known as
vulcanization, from roman god of fire Vulcan
Vulcanization - connects the strands through
links of sulfur so that the interconnected
polyisoprene molecules retain their orientation
when heated and stretched
Christian Schoenbein - accidentally invented
guncotton by spilling a mixture of nitric acid and
sulfuric acid
John Wesley Hyatt and his brother Isaiah -
consciously made an artificial ivory, now called
celluloid
Celluloid - a thermoplastic used for dental
plates, photographic film, brush handles,
detachable collars, ping pong balls
Leo Hendrik Baekeland - an active, productive
and successful industrial chemist and the
inventor of Bakelite
Bakelite - a condensation polymer and a
thermosetting plastic
-forms as phenol and formaldehyde polymerizes
-a hard, sturdy material resistant to heat and
electricity
-chemical formula: (C6-H6-O.C-H2-O)x
Reasons why discoveries through accidents
on hot kitchen stoves came to an end:
-the growing sophistication of scientific
equipment and techniques
-the increasing rigor of research programs
carried out in academic, industrial and
institutional laboratories, and
-the development, in the 1920s, of a
comprehensive understanding of the molecular
structure of polymers
Polyolefins - polymers produced by the
polymerization of alkenes and compounds
closely related to them
Olefin - another and much older name for the
unsaturated hydrocarbons we now know as
alkenes
Polystyrene - thermoplastic, used for
inexpensive, clear rigid drinking glasses
-high-impact polystyrene: sturdy furniture,
inexpensive tableware, stereo, television and
computer cabinets
-solid lightweight polystyrene foams: good
thermal insulators and shock absorbers for
picnic coolers, egg cartoons, clamshell
containers for fast foods, disposable cups
Styrofoam - made by using a gas to generate a
foam of liquid polystyrene
Vinyl - in the real of consumer products, means
a tough, flexible, and often smooth shiny plastics
as a substitute for leather
-to the chemist, represents a hydrocarbon group
formed by the removal of a hydrogen atom from
ethylene
-poly(vinyl chloride), polyvinylchloride and PVC
serve as names for the thermoplastic formed by
the addition polymerization of vinyl chloride
-forms a tough plastic for pipes, plumbing,
electric conduit, flooring, and both indoor and
outdoor wall coverings, molding toys, garden
hoses and phonograph records
Plasticizer - liquid mixed with a plastic to soften
it
Addition Polymers:
-ethylene - polyethylene
-vinyl chloride - poly(vinyl chloride),
polyvinylchloride, PVC
-vinyl acetate - poly(vinyl acetate),
polyvinylacetate, PVA
-acrylonitrile - polyacronitrile, Orlon, Acrilan,
Creslan
-viniylidine chloride - poly(vinylidine chloride),
Saran
-tetrafluoroethylene - polytetrafluoroethylene,
Teflon
-methyl methacrylate - poly(methacrylate),
Lucite, Plexiglas
Saran: barrier to food odors
Teflon: coating for bearings, valve seats,
gaskets
Lucite and Plexiglas: glasses, camera lenses,
optical equipment, costume jewelry
Low-density polyethylene (LDPE) - low-
density, soft, waxy, flexible, relatively low-
melting plastic
-disorganized polymeric strands
-producing trash bags
High-density polyethylene (HDPE) - denser,
harder, higher melting and more rigid polymer
-aligned into localized areas of tightly packed
strands (organometallic catalysts)
-manufacture of bottles, containers
Three different ways methyl groups can be
arranged:
1. They can all protrude from the same side of
stretched-out, zig-zag molecular chain (isotactic
polymer)
2. They can appear on alternating sides
(syndiotactic polymer)
3. They can be oriented randomly (atactic
polymer)
The term for the three orientations comes from
greek word - taktos, “ordered” which is modified
by prefixes iso- (same), syndio- (two together)
and a- (not)
Giullo Natta and Karl Zieger - shared a Nobel
prize in chemistry for preparing stereochemically
ordered polymers
Poly(ethylene terephthalate) or PET - leading
polyester in condensation polymers
-forms thin, tough films - Mylar
-Dacron in United States, Terylene in Great
Britain
John Rex Whinfield - succeeded in producing
PET by polymerizing a mixture of ethylene
glycol and terephtalic acid
Rayon - generic term of fibers that are all
derived from cellulose
Homopolymer neoprene - comes from the
polymerization of chloropene
Copolymer styrene-butadiene rubber -
leading synthetic elastomer
Silicon dioxide - one of most important polymer
of all
-makes up the clay, rocks and inorganic soils of
the earth’s crust
Deoxyribonucleic acid or DNA - one of most
important polymer of all
-polymeric acid that resides in the nucleus of
every cell and that carries in its structure the
genetic code. (copolymer)
Genetic code - the genetic information
contained in the sequence of four bases strung
out along the polymeric nucleic acid, DNA
Biodegradable - if microorganisms within the
environment can convert it to simpler
substances that form our natural environment
Plastic litter - lies by the side of the road,
unchanged by weather or microorganisms
Incineration - alternative approach for dealing
with plastic trash
Telfon, poly(vinyl chloride), poly (vinylidene
chloride) - produces irritating or toxic gases as
they burn
Recycling and Degradability - two possible
routes offered by Science and Technology
Plastic lumber - low-grade product as
substitute for wood