BIBLIOGRAPHY
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General References
L. I. Nass, ed., Encyclopedia of PVC, Vol. 1 (1976), Vol. 2 (1977),
Vol. 3 (1977), Marcel Dekker, New York.
W. S. Penn, PVC Technology, MacLaren, London, 1966.
J. H. Briston and L. L. Katan, Plastic Films, Longman, New York,
1983.
POLY(LACTIC ACID)
RAFAEL AURAS
School of Packaging, Michigan
State University, East Lansing,
Michigan
INTRODUCTION
Poly(lactic acid) (PLA) polymers are biodegradable polye-
sters derived from lactic acid (LA) or 2-hydroxy propionic
acid, which is generally obtained by bacterial fermenta-
tion of carbohydrates from agricultural crops such as corn,
potato, and cassava. PLA has been used extensively for
medical applications since the 1970s because of its bior-
esorbable and biocompatible properties in the human
body. Its use in packaging and textile applications until
now has been scarce because of its high initial costs.
However, discoveries of new polymerization pathways
and advances in manufacturing technologies have drama-
tically lowered PLA costs (1–5). PLA was approved by the
U.S. Food & Drug Administration for use in contact with
foods in 1992 (6), PLA resin can be produced entirely from
biomass, and the final products can safely be recycled,
composted, or incinerated (2). PLA has been recognized by
industries, consumers, and governments as a candidate
material to help in reducing the municipal solid waste
produced by packaging and containers (7).
To date, the production of PLA has reached a large-
scale industrial capacity (75 metric kt in 2007 and is
expected to reach 325 metric kt by 2010), which makes it
the most important biopolyester produced from renewable
resources (4). NatureWorks LLC (Blair, NE), the former
Cargill Inc., and Dow joint venture, which is nowadays
owned by Cargill Inc. and Teijin Ltd., produces the largest
amount of commercially available PLA resins with a total
production of 140 ktpa as of January 2009. Nature Works
is also planning to start building a second plant. Toyota
has produced special PLAs since 2003 for automotive
applications. Galactic and Total Petrochemicals, Uhde
Inventa Fischer, and Pyramide Bioplastics have an-
nounced plans to produce commercial PLA by the end of
2009. PURAC and Sulzer have also announced joint
efforts to produce PLA from solid lactide to obtain ex-
panded PLA beads to target the market of expanded
polystyrene (PS). Additional development of stereocom-
plex PLA by PURAC, Musashino Chemical Laboratory,
and Teijin has gained attention for the production of a 50/
50 blend of poly(L-lactic acid) PLLA and poly(D-lactic
acid) PDLA with a high melting point targeting fiber
applications. More pilot scale plants to produce PLA
have been announced in China, and currently, PURAC
has expanded its lactic acid capacity targeting the in-
crease of PLA demand (2, 4).
PRODUCTION OF HIGH-MOLECULAR-WEIGHT PLA
The main constitutional unit of PLA is lactic acid. LA can
exist in two main optical configurations: L or D. PLA
polymers can be produced with varying degrees of L or D
lactic acid. According to its molecular composition, PLA can
be named as poly(XY-lactic acid), in which X and/or Y are
the amount of L and D lactic acid, respectively. D lactic acid
mainly comes from the racemic lactic acid (LD configura-
tion). So, a PLA polymer’s label as poly(96% L-lactic acid)
will be composed of 96% L-lactic acid and 4% D lactic acid.
PLA is mainly produced by three synthesis processes:
(a) polymerization through lactide formation, (b) direct
condensation polymerization, and (c) azeotropic dehydra-
tion condensation (see Scheme 1). Ring open polymeriza-
tion process is the technology producing the most amount
POLY(LACTIC ACID) 967