CompTox Dashboard (EPA)
|Melting point||150 to 160 °C (302 to 320 °F; 423 to 433 K)|
|0 mg/ml |
|NFPA 704 (fire diamond)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Polylactic acid, also known as poly(lactic acid) or polylactide (abbreviation PLA) is a thermoplastic polyester with backbone formula (C
n or [–C(CH
n, formally obtained by condensation of lactic acid C(CH
3)(OH)HCOOH with loss of water (hence its name). It can also be prepared by ring-opening polymerization of lactide [–C(CH
2, the cyclic dimer of the basic repeating unit.
PLA has become a popular material due to it being economically produced from renewable resources. In 2010, PLA had the second highest consumption volume of any bioplastic of the world, although it is still not a commodity polymer. Its widespread application has been hindered by numerous physical and processing shortcomings. PLA is the most widely used plastic filament material in 3D printing.
Although the name "polylactic acid" is widely used, it does not comply with IUPAC standard nomenclature, which is "poly(lactic acid)". The name "polylactic acid" is potentially ambiguous or confusing, because PLA is not a polyacid (polyelectrolyte), but rather a polyester.
Several industrial routes afford usable (i.e. high molecular weight) PLA. Two main monomers are used: lactic acid, and the cyclic di-ester, lactide. The most common route to PLA is the ring-opening polymerization of lactide with various metal catalysts (typically tin octoate) in solution or as a suspension. The metal-catalyzed reaction tends to cause racemization of the PLA, reducing its stereoregularity compared to the starting material (usually corn starch).
The direct condensation of lactic acid monomers can also be used to produce PLA. 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. The condensation reaction is reversible and subject to equilibrium, so removal of water is required to generate high molecular weight species. Water removal by application of a vacuum or by azeotropic distillation is required to drive the reaction toward polycondensation. 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. Molecular weights of 128–152 kDa are obtainable thus.
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. 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 a co-product.
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). PLA is soluble in solvents, hot benzene, tetrahydrofuran, and dioxane.
Physical and mechanical properties
PLA polymers range from amorphous glassy polymer to semi-crystalline and highly crystalline polymer with a glass transition 60–65 °C, a melting temperature 130-180 °C, and a Young's modulus 2.7–16 GPa. Heat-resistant PLA can withstand temperatures of 110 °C. The basic mechanical properties of PLA are between those of polystyrene and PET. The melting temperature of PLLA can be increased by 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 1:1 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. The flexural modulus of PLA is higher than polystyrene and PLA has good heat sealability.
Several technologies such as annealing, adding nucleating agents, forming composites with fibers or nano-particles, chain extending and introducing crosslink structures have been used to enhance the mechanical properties of PLA polymers. Polylactic acid can be processed like most thermoplastics into fiber (for example, using conventional melt spinning processes) and film. PLA has similar mechanical properties to PETE polymer, but has a significantly lower maximum continuous use temperature. With high surface energy, PLA has easy printability which makes it widely used in 3-D printing. The tensile strength for 3-D printed PLA was previously determined.
There is also poly(L-lactide-co-D,L-lactide) (PLDLLA) – used as PLDLLA/TCP scaffolds for bone engineering. Poly l lactic acid is also used to stimulate collagen synthesis in fibroblast via foreign body reaction in the presence of macrophage. Macrophage acts as a stimulant in secretion of cytokines and mediators such as TGFβ etc which stimulate the fibroblast to secrete collagen into the surrounding tissue. Therefore, poly l lactic acid can have potential application in the dermatological studies  
Organic solvents for PLA
PLA is soluble in a range of organic solvents. Ethyl acetate, due to its ease of access and low risk of use, is of most interest. PLA 3D printer filament dissolves when soaked in ethyl acetate, making it a useful solvent for cleaning 3D printing extruder heads or removing PLA supports. The boiling point of ethyl acetate is low enough to also smooth PLA in a vapor chamber, similar to using acetone vapor to smooth ABS.
Other safe solvents to use include propylene carbonate, which is safer than ethyl acetate but is difficult to purchase commercially. Pyridine can also be used however this is less safe than ethyl acetate and propylene carbonate. It also has a distinct bad fish odor.
PLA is used as a feedstock material in desktop fused filament fabrication 3D printers (e.g. RepRap). PLA-printed solids can be encased in plaster-like moulding materials, then burned out in a furnace, so that the resulting void can be filled with molten metal. This is known as "lost PLA casting", a type of investment casting.
PLA can degrade into innocuous lactic acid, so it is used as medical implants in the form of anchors, screws, plates, pins, rods, and as a mesh. Depending on the exact type used, it breaks down inside the body within 6 months to 2 years. This gradual degradation is desirable for a support structure, because it gradually transfers the load to the body (e.g. the bone) as that area heals. The strength characteristics of PLA and PLLA implants are well documented.
PLA can also be used as a decomposable packaging material, either cast, injection-molded, or spun. Cups and bags have been made from this material. In the form of a film, it shrinks upon heating, allowing it to be used in shrink tunnels. It is useful for producing loose-fill packaging, compost bags, food packaging, and disposable tableware. In the form of fibers and nonwoven fabrics, PLA also has many potential uses, for example as upholstery, disposable garments, awnings, feminine hygiene products, and diapers. Thanks to its bio-compatibility and biodegradability, PLA has also found ample interest as a polymeric scaffold for drug delivery purposes.
Racemic and regular PLLA has a low glass transition temperature, which is undesirable. A stereocomplex of PDLA and PLLA has a higher glass transition temperatures, lending it more mechanical strength. It has 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. Pure poly-L-lactic acid (PLLA), on the other hand, is the main ingredient in Sculptra, a long-lasting facial volume enhancer, primarily used for treating lipoatrophy of cheeks. Progress in biotechnology has resulted in the development of commercial production of the D enantiomer form, something that was not possible until recently.
Tea bags made of PLA. Peppermint tea is enclosed.
3D printed human skull with data from computed tomography. Transparent PLA.
PLA is degraded abiotically by three mechanisms:
- Hydrolysis: The ester groups of the main chain are cleaved, thus reducing molecular weight.
- Thermal degradation: A complex phenomenon leading to the appearance of different compounds such as lighter molecules and linear and cyclic oligomers with different Mw, and lactide.
- Photodegradation: UV radiation induces degradation. This is a factor mainly where PLA is exposed to sunlight in its applications in plasticulture, packaging containers and films.
The hydrolytic reaction is:
The degradation rate is very slow in ambient temperatures. A 2017 study found that at 25 °C in seawater, PLA showed no loss of mass over a year, but the study did not measure breakdown of the polymer chains or water absorption. As a result, it degrades poorly in landfills and household composts, but is effectively digested in hotter industrial composts, usually degrading best at temperatures of over 60°C.
Pure PLA foams are selectively hydrolysed in Dulbecco's modified Eagle's medium (DMEM) supplemented with fetal bovine serum (FBS) (a solution mimicking body fluid). After 30 days of submersion in DMEM+FBS, a PLLA scaffold lost about 20% of its weight.
PLA can also be degraded by some bacteria, such as Amycolatopsis and Saccharothrix. A purified protease from Amycolatopsis sp., PLA depolymerase, can also degrade PLA. Enzymes such as pronase and most effectively proteinase K from Tritirachium album degrade PLA.
End of life
Four possible end-of-life scenarios are the most common:
- Recycling: which can be either chemical or mechanical. Currently, the SPI resin identification code 7 ("others") is applicable for PLA. In Belgium, Galactic started the first pilot unit to chemically recycle PLA (Loopla). Unlike mechanical recycling, waste material can hold various contaminants. Polylactic acid can be chemically recycled to monomer by thermal depolymerization or hydrolysis. When purified, the monomer can be used for the manufacturing of virgin PLA with no loss of original properties  (cradle-to-cradle recycling).[dubious ] End-of-life PLA can be chemically recycled to methyl lactate by transesterification.
- Composting: PLA is biodegradable under industrial composting conditions, starting with chemical hydrolysis process, followed by microbial digestion, to ultimately degrade the PLA. Under industrial composting conditions (58 °C), PLA can partly (about half) decompose into water and carbon dioxide in 60 days, after which the remainder decomposes much more slowly, with the rate depending on the material's degree of crystallinity. Environments without the necessary conditions will see very slow decomposition akin to that of non-bioplastics, not fully decomposing for hundreds or thousands of years.
- Incineration: PLA can be incinerated without producing chlorine-containing chemicals or heavy metals because it contains only carbon, oxygen, and hydrogen atoms. Since it does not contain chlorine it does not produce dioxins during incineration.
- Landfill: the least preferable option is landfilling because PLA degrades very slowly in ambient temperatures, often as slowly as other plastics.
- Acrylonitrile butadiene styrene (ABS) - also used for 3D printing
- Cellophane, polyglycolide, plastarch material, poly-3-hydroxybutyrate – biologically derived polymers
- Zein, shellac – biologically derived coating materials
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