Ingeniero Tecnico

Polylactic acid
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Polylactic acid |
|
Identifiers |
CAS number | 33135-50-1 |
Properties |
Molecular formula | (C3H4O2)n |
Density | 1210-1430 kg/m3 [1] |
Melting point | 150-160 °C [1] |
Solubility in water | Insoluble in Water [2] |
Hazards |
NFPA 704 | 100 |
Except where noted otherwise, data are givenfor materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Polylactic acid or polylactide (PLA) is a thermoplastic aliphatic polyester derived from renewable resources, such as corn starch (in the United States), tapioca roots, chips or starch (mostly in Asia), or sugarcane (in the rest of the world).
The name "polylactic acid" does not comply with IUPAC standardnomenclature, and is potentially ambiguous or confusing, because PLA is not a polyacid (polyelectrolyte), but rather a polyester.[citation needed]
Contents [hide]  * 1 Production * 1.1 Manufacturers * 2 Chemical and physical properties * 3 Applications * 4 Recycling * 5 See also * 6 References * 7 External links |
[edit] Production
There are several industrial routes to usable(i.e. high molecular weight) poly(lactic acid). Two main monomers are used: lactic acid, and the cyclic di-ester, lactide. The most common route to poly(lactic acid) is the ring-opening polymerization of lactide with various metal catalysts (typically tin octoate) in solution, in the melt, or as a suspension. The metal-catalyzed reaction tends to cause racemization of the poly(lactic acid), reducingits stereoregularity compared to the starting material.[3]
Another route to poly(lactic acid) is the direct condensation of lactic acid monomers. This process needs to be carried out at less than 200 °C; above that temperature, the entropically favored lactide monomer is generated. This reaction generates one equivalent of water for every condensation (esterification) step, and that is undesirablebecause water causes chain-transfer leading to low molecular weight material. The direct condensation is thus performed in a stepwise fashion, where lactic acid is first oligomerized to PLA oligomers. Thereafter, polycondensation is done in the melt or as a solution, where short oligomeric units are combined to give a high molecular weight polymer strand. Water removal by application of a vacuumor by azeotropic distillation is crucial to favor polycondensation over transesterification. Molecular weights of 130 kDa can be obtained this way. Even higher molecular weights can be attained by carefully crystallizing the crude polymer from the melt. Carboxylic acid and alcohol end groups are thus concentrated in the amorphous region of the solid polymer, and so they can react. Molecularweights of 128-152 kDa are obtainable thus.[3]

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 Lenantiomers used, and to a lesser extent on the type of catalyst used. Apart from lactic acid and lactide, lactic acid O-carboxyanhydride ("lac-OCA"), a five-membered cyclic compound has been used academically as well. This compound is more reactive than lactide, because its polymerization is driven by the loss of one equivalent of carbon dioxide per equivalent of lactic acid. Water is not aco-product.[4]
The direct biosynthesis of poly(lactic acid) similar to the poly(hydroxyalkanoate)s has been reported as well.[5]
[edit] Manufacturers
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...