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Polylactic acid
From Wikipedia, the free encyclopedia Navigation Main page Contents Featured content Current events Random article Donate to Wikipedia 1 Synthesis 2 Chemical and physical properties Help About Wikipedia Community portal Recent changes Contact Wikipedia 3 Applications 4 Production 5 PLA Recycling 6 Recycling code 7 See also 7.1 Other biodegradable polymers Toolbox What links here Related changes Upload file Special pages Permanent link Cite this page 8 References 9 External links
The skeletal formula of poly(lactic acid)

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

Interaction

Synthesis

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Catalytic and thermolytic ring-opening polymerization of lactide (left) to polylactide (right)

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Bacterial fermentation is used to produce lactic acid from corn starch or cane sugar. However, lactic acid cannot be directly polymerized to a useful product, because each polymerization reaction generates one molecule of water, the presence of which degrades the forming polymer chain to the point that only very low molecular weights are observed. Instead, two lactic acid molecules undergo a single esterfication and then catalytically cyclized to make a cyclic dilactate ester. Although dimerization also generates water, it can be separated prior to polymerization due to a significant drop in polarity. PLA of high molecular weight is produced from the dilactate ester by ring-opening polymerization using most commonly a stannous octoate [citation needed] catalyst, but for laboratory demonstrations tin(II) chloride is often employed. This mechanism does not generate additional water, and hence, a wide range of molecular weights is accessible. 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 stereospecific catalysts can lead to heterotactic PLA which has been found to show crystallinity. The degree of crystallinity, and hence many 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.

Chemical and physical properties

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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
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

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enabling use in higher value application area's. waste material can hold various contaminants. the stereocomplex is blended with a rubber-like polymer such as ABS). PLA is a sustainable alternative to petrochemical-derived products.000 tons lactide plant at their production site in Thailand (Rayong Province). Unlike mechanical recycling. Purac has developed the technology to polymerize these lactides with Sulzer. the monomers for PLA production. Through thermal depolymerization. a Swiss Engineering company. In a tripartite collaboration between Purac. PLA has been used as the hydrophobic block of amphiphilic synthetic block copolymers used to form the vesicle membrane of polymersomes. Progress in biotechnology has resulted in the development of commercial production of the D enantiomer form. food packaging. 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". Recycling code [edit] Currently. and disposable tableware. It is also being evaluated as a material for tissue engineering. a hemp fiber building insulation. that is developing a second generation of polylactic acid product. NatureWorks was the primary producer of PLA (bioplastic) in the United States. while in March 2010 the construction has started of a 75. In the form of fibers and nonwoven textiles. clamshells for food packaging. feminine hygiene products. Studies have shown that on standing. [13][14] See also Polymerization PLA film [edit] Other biodegradable polymers Cellophane Plastarch material [edit] . 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). a State Senate bill in California (SB 898) [12] proposed the marking of PLA with a new "0" code. dialysis media and drug delivery devices. Because it is biodegradable.a shorter polymer of lactic acid) in pressurized metered dose inhalers (pMDIs) as a surfactant. PLA cups cannot hold hot liquids. making them useful for low-end packaging applications. awnings. PLA has also been developed in the United Kingdom to serve as sandwich packaging. disposable garments. including PLA. something that was not possible until recently. this part of the bill was removed before passage. an attractive biodegradable and/or biobased alternative to EPS-foam in avariety of application areas. PLA is used for biodegradable and compostable disposable cups for cold beverages. The primary producer of PDLLA is PURAC. Thanks to the availability of D-lactide. hot-fill applications and even engineering plastics (in this case. Such blends also have good formstability and visual transparency. the lining in cups for hot beverages. Purac partners will be able to use stereo-complex technologies to produce new PLA grades with heat-stability (HDT) up to 180 degrees C. Sulzer and Synbra solutions were developed to allow Synbra to start production of PLA and subsequently E-PLA. PLA is more expensive than many petroleum-derived commodity plastics. microwavable trays. compost bags. Purac has developed a unique business model by starting production of Lactides (D and L. Galactic started the first pilot unit to chemically recycle PLA (Loopla). it can also be employed in the preparation of bioplastic. such as sutures. Purac collaborates with various PLA production partners to develop production scale and new markets for PLA. The demand for corn is growing. [7] Due to PLA's relatively low glass transition temperature.Stereocomplex blends of PDLA and PLLA have a wide range of applications. Futerro.[11] Since 2009. but its price has been falling as production increases. The Korean research center KAIST has announced that they have found a way to produce PLA using bio-engineered Escherichia coli. and diapers. Production As of Jun 2010. for example as upholstery. a wholly owned subsidiary of [CSM] located in the Netherlands. in their Spanish production plant with a capacity of several thousands of tons. [edit] Galactic and Total Petrochemicals operate a joint-venture. PLA also has many potential uses. or other carbohydrate-rich substances like maize. such as woven shirts (ironability). pMDIs without OLA will yield a much higher dose than intended as compared to those containing OLA which delivers a fairly constant dosage [8]. However. deli containers and The pharmaceutical industry uses oligolactic acid (OLA . [4] PLA is currently used in a number of biomedical applications. stents. SPI Resin identification code 7 is applicable. both due to the use of corn for bioethanol and for corn-dependent commodities. Other companies involved in PLA manufacturing are PURAC Biomaterials (The Netherlands) and several Chinese manufacturers. PLA Recycling [edit] In Belgium. PLA is used as a feedstock material in 3D printers such as Reprap [9] and Makerbot [10]. sugar or wheat. This project includes the building of a PLA pilot plant of 1500 tonnes/year in Belgium. [6] PLA has also been used in France to serve as the binder in Isonat Nat’isol. since the lactides from which it is ultimately produced can be derived from the fermentation of agricultural by-products such as corn starch [5] Biodegradable plastic cups in use at an eatery. In 2007. useful for producing loose-fill packaging.

^ Södergård. a non-profit organization. ^ Middelton.cagreen. Smithsonian Magazine .com/news178178601. Anders. Elizabeth (August 2006). FP International Your plastic pal.manufacturingtalk.cawrecycles.Module 2. ^ Compare Materials: PLA and PETE ^ http://www..html ^ http://www.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 ^ http://www. 4. John C. CSU. The Economist article Categories: Biodegradable plastics | Bioplastics | Polyesters | Synthetic fibers | Transparent materials | Thermoplastics [edit] This page was last modified on 11 January 2011 at 18:33.com/pla ^ http://edition.1016/S0142-9612(00)00101 -0. (2010). Progress in Polymer Science 27: 1123–1163. Ross. Contact us Privacy policy About Wikipedia Disclaimers . Tipton (2000).ca ^ Kennedy.Polycaprolactone Polyglycolide Poly-3-hydroxybutyrate Zein References This article needs additional citations for verification. 13. 8.korea. Unsourced material may be challenged and removed . Wikipedia® is a registered trademark of the Wikimedia Foundation. Text is available under the Creative Commons Attribution-ShareAlike License. 10. (March 2008) [edit] 1. 14.leginfo. "Properties of lactic acid based polymers and their correlation with composition". doi:10. "Corn Plastic to the Rescue".AMENDED External links New polymerization technology for PLA developed White paper on the Science of Biodegradable Plastics. ^ http://www. Inc. See Terms of Use for details. Australia ^ http://reprap.org/wiki/PLA ^ http://wiki. 9. "Synthetic biodegradable polymers as orthopedic devices".org/issues/current_legislation/sb898_07 Bill summary from Californians Against Waste. 5.makerbot. Mikael Stolt (February 2002).cnn. Pharmaceutics 2 .physorg.ca.plastic/index. 12.com/news/trj/trj110.1016/S0079-6700(02)00012 -6.com/2009/TECH/science/11/23/eco. Arthur J. 3. doi:10. Biomaterial 21: 2335–2346.. an environmental group ^ SB 898 Senate Bill . additional terms may apply. 11. 7.html Koreans make plastics without fossil fuel chemicals ^ http://www. 6. Please help improve this article by adding reliable references .html ^ Royte. Retrieved 2008-03-06. 2.

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