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Polylactic acid
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Poly(lactic acid) or polylactide (PLA) is a thermoplastic aliphatic polyester derived from renewable
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resources, such as corn starch (in the United States), tapioca products (roots, chips or starch mostly in
Main page Asia) or sugarcanes (in the rest of world). It can biodegrade under certain conditions, such as the
Contents presences of oxygen and is difficult to recycle.
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The name "polylactic acid" is to be used with caution, not complying to standard nomenclatures (such as
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IUPAC) and potentially leading to ambiguity (PLA is not a polyacid (polyelectrolyte), but rather a polyester)
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Contents

Interaction 1 Synthesis
2 Chemical and physical properties
Help 3 Applications The skeletal formula of poly(lactic
About Wikipedia acid)
4 Production
Community portal 5 PLA Recycling
Recent changes 6 Recycling code
Contact Wikipedia 7 See also
7.1 Other biodegradable polymers
Toolbox 8 References
9 External links
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Synthesis [edit]
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Catalytic and thermolytic ring-opening polymerization of lactide (left) to polylactide (right)

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‫ﺔﻴﺑﺮﻌﻟﺍ‬ Bacterial fermentation is used to produce lactic acid from corn starch or cane sugar. However, lactic acid cannot be directly polymerized to a useful
Deutsch product, because each polymerization reaction generates one molecule of water, the presence of which degrades the forming polymer chain to the
Español point that only very low molecular weights are observed. Instead, two lactic acid molecules undergo a single esterfication and then catalytically
Esperanto cyclized to make a cyclic dilactate ester. Although dimerization also generates water, it can be separated prior to polymerization due to a
Français significant drop in polarity. PLA of high molecular weight is produced from the dilactate ester by ring-opening polymerization using most commonly
Italiano a stannous octoate [citation needed] catalyst, but for laboratory demonstrations tin(II) chloride is often employed. This mechanism does not generate
Nederlands additional water, and hence, a wide range of molecular weights is accessible.
日本語 Polymerization of a racemic mixture of L- and D-lactides usually leads to the synthesis of poly-DL-lactide (PDLLA) which is amorphous. Use of
Polski
stereospecific catalysts can lead to heterotactic PLA which has been found to show crystallinity. The degree of crystallinity, and hence many
Русский
important properties, is largely controlled by the ratio of D to L enantiomers used, and to a lesser extent on the type of catalyst used.
Svenska
中文 Chemical and physical properties [edit]

Due to the chiral nature of lactic acid, several distinct forms of polylactide exist: poly-L-lactide (PLLA) is the product resulting from polymerization
of L,L-lactide (also known as L-lactide). PLLA has a crystallinity of around 37%, a glass transition temperature between 60-65 °C, a melting
temperature between 173-178 °C and a tensile modulus between 2.7-16 GPa [1][2].
PLA has similar mechanical properties to PETE polymer, but has a significantly lower maximum continuous use temperature. [3]
Polylactic acid can be processed like most thermoplastics into fiber (for example using conventional melt spinning processes) and film. The melting
temperature of PLLA can be increased 40-50 °C and its heat deflection temperature can be increased from approximately 60°C to up to 190 °C by
physically blending the polymer with PDLA (poly-D-lactide). PDLA and PLLA form a highly regular stereocomplex with increased crystallinity. The
temperature stability is maximised when a 50:50 blend is used, but even at lower concentrations of 3-10% of PDLA, there is still a substantial
improvement. In the latter case, PDLA acts as a nucleating agent, thereby increasing the crystallization rate. Biodegradation of PDLA is slower
than for PLA due to the higher crystallinity of PDLA. PDLA has the useful property of being optically transparent.

Applications [edit]

Stereocomplex blends of PDLA and PLLA have a wide range of applications, such as woven shirts
(ironability), microwavable trays, hot-fill applications and even engineering plastics (in this case, the
Stereocomplex blends of PDLA and PLLA have a wide range of applications, such as woven shirts
(ironability), microwavable trays, hot-fill applications and even engineering plastics (in this case, the
stereocomplex is blended with a rubber-like polymer such as ABS). Such blends also have good form-
stability and visual transparency, making them useful for low-end packaging applications. Progress in
biotechnology has resulted in the development of commercial production of the D enantiomer form,
something that was not possible until recently. [4]
PLA is currently used in a number of biomedical applications, such as sutures, stents, dialysis media
and drug delivery devices. It is also being evaluated as a material for tissue engineering. Because it is
biodegradable, it can also be employed in the preparation of bioplastic, useful for producing loose-fill Biodegradable plastic cups in use at an
packaging, compost bags, food packaging, and disposable tableware. In the form of fibers and non- eatery.
woven textiles, PLA also has many potential uses, for example as upholstery, disposable garments,
awnings, feminine hygiene products, and diapers.
PLA has been used as the hydrophobic block of amphiphilic synthetic block copolymers used to form
the vesicle membrane of polymersomes.
PLA is a sustainable alternative to petrochemical-derived products, since the lactides from which it is
ultimately produced can be derived from the fermentation of agricultural by-products such as corn starch
[5]
or other carbohydrate-rich substances like maize, sugar or wheat.
PLA is more expensive than many petroleum-derived commodity plastics, but its price has been falling
as production increases. The demand for corn is growing, both due to the use of corn for bioethanol and
for corn-dependent commodities, including PLA.
Due to PLA's relatively low glass
PLA has also been developed in the United Kingdom to serve as sandwich packaging. [6] transition temperature, PLA cups cannot
hold hot liquids.
PLA has also been used in France to serve as the binder in Isonat Nat’isol, a hemp fiber building
insulation.
PLA is used for biodegradable and compostable disposable cups for cold beverages, the lining in cups for hot beverages, deli containers and
clamshells for food packaging. [7]
The pharmaceutical industry uses oligolactic acid (OLA - a shorter polymer of lactic acid) in pressurized metered dose inhalers (pMDIs) as a
surfactant. Studies have shown that on standing, pMDIs without OLA will yield a much higher dose than intended as compared to those containing
OLA which delivers a fairly constant dosage [8].
PLA is used as a feedstock material in 3D printers such as Reprap [9] and Makerbot [10].

Production [edit]

As of Jun 2010, NatureWorks was the primary producer of PLA (bioplastic) in the United States.
Other companies involved in PLA manufacturing are PURAC Biomaterials (The Netherlands) and several Chinese manufacturers. The primary
producer of PDLLA is PURAC, a wholly owned subsidiary of [CSM] located in the Netherlands.
Galactic and Total Petrochemicals operate a joint-venture, Futerro, that is developing a second generation of polylactic acid product. This project
includes the building of a PLA pilot plant of 1500 tonnes/year in Belgium.

The Korean research center KAIST has announced that they have found a way to produce PLA using bio-engineered Escherichia coli.[11]
Since 2009, Purac has developed a unique business model by starting production of Lactides (D and L, the monomers for PLA production, in their
Spanish production plant with a capacity of several thousands of tons, while in March 2010 the construction has started of a 75.000 tons lactide
plant at their production site in Thailand (Rayong Province). Purac has developed the technology to polymerize these lactides with Sulzer, a Swiss
Engineering company. Purac collaborates with various PLA production partners to develop production scale and new markets for PLA. Thanks to
the availability of D-lactide, Purac partners will be able to use stereo-complex technologies to produce new PLA grades with heat-stability (HDT) up
to 180 degrees C, enabling use in higher value application area's. In a tripartite collaboration between Purac, Sulzer and Synbra solutions were
developed to allow Synbra to start production of PLA and subsequently E-PLA, an attractive biodegradable and/or biobased alternative to EPS-foam
in avariety of application areas. This collaboration was awarded by Frost and Sullivan with the Innovation of the Year Award in 2008 citing "This
unique offering will significantly reduce the process and product development time enabling faster and more reliable market entry for PLA
producers".

PLA Recycling [edit]

In Belgium, Galactic started the first pilot unit to chemically recycle PLA (Loopla). Unlike mechanical recycling, waste material can hold various
contaminants. Through thermal depolymerization, a highly purified lactic acid is extracted and can be considered as raw material for the
manufacturing of virgin PLA with no loss of original properties (cradle-to-cradle recycling).

Recycling code [edit]

Currently, SPI Resin identification code 7 is applicable. In 2007, a State Senate bill in California (SB 898) [12] proposed the marking of PLA with a
new "0" code. However, this part of the bill was removed before passage. [13][14]

See also [edit]

Polymerization
PLA film

Other biodegradable polymers [edit]

Cellophane
Plastarch material
 Polycaprolactone
Polyglycolide
Poly-3-hydroxybutyrate
Zein

References [edit]

This article needs additional citations for verification.

Please help improve this article by adding reliable references . Unsourced material may be challenged and removed . (March
2008)

1. ^ Södergård, Anders; Mikael Stolt (February 2002). "Properties of lactic acid based polymers and their correlation with composition". Progress in
Polymer Science 27: 1123–1163. doi:10.1016/S0079-6700(02)00012 -6.
2. ^ Middelton, John C.; Arthur J. Tipton (2000). "Synthetic biodegradable polymers as orthopedic devices". Biomaterial 21: 2335–2346.
doi:10.1016/S0142-9612(00)00101 -0.
3. ^ Compare Materials: PLA and PETE
4. ^ http://www.physorg.com/news178178601.html
5. ^ Royte, Elizabeth (August 2006). "Corn Plastic to the Rescue". Smithsonian Magazine . Retrieved 2008-03-06.
6. ^ http://www.manufacturingtalk.com/news/trj/trj110.html
7. ^ http://www.cagreen.ca
8. ^ Kennedy, Ross. (2010). Pharmaceutics 2 - Module 2. CSU. Australia
9. ^ http://reprap.org/wiki/PLA
10. ^ http://wiki.makerbot.com/pla
11. ^ http://edition.cnn.com/2009/TECH/science/11/23/eco.korea.plastic/index.html Koreans make plastics without fossil fuel chemicals
12. ^ http://www.leginfo.ca.gov/cgi-bin/postquery?bill_number=sb_898&sess=CUR&house=B&author=simitian Full text and version history of California
State Senate Bill 898
13. ^ http://www.cawrecycles.org/issues/current_legislation/sb898_07 Bill summary from Californians Against Waste, an environmental group
14. ^ SB 898 Senate Bill - AMENDED

External links [edit]

New polymerization technology for PLA developed

White paper on the Science of Biodegradable Plastics, FP International
Your plastic pal, The Economist article

Categories: Biodegradable plastics | Bioplastics | Polyesters | Synthetic fibers | Transparent materials | Thermoplastics

This page was last modified on 11 January 2011 at 18:33.

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