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Production
Except where otherwise noted, data
The monomer is typically from fermented plant starch such as are given for materials in their
standard state (at 25 °C [77 °F],
from corn, cassava, sugarcane or sugar beet pulp. 100 kPa).
Several industrial routes afford usable (i.e. high molecular Infobox references
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).[6]
Another route to PLA 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.
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.[6]
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.[7]
The direct biosynthesis of PLA similar to the poly(hydroxyalkanoate)s has been reported as well.[8]
Another method devised is by contacting lactic acid with a zeolite. This condensation reaction is a one-
step process, and runs about 100 °C lower in temperature.[9][10]
Materials properties
Chemical properties
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.[11]
Several technologies such as annealing,[16][17][18] adding nucleating agents, forming composites with
fibers or nano-particles,[19][20][21] chain extending[22][23] 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.[24] 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.[25]
Solvent welding
PLA can be solvent welded using dichloromethane.[28]
Applications
PLA is used as a feedstock material in desktop fused filament fabrication 3D printers (e.g.
RepRap).[30][31] 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.[32]
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.[33] 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.[34]
PLA can also be used as a decomposable packaging material, either cast, injection-molded, or spun.[33]
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.[35]
Mulch film made of PLA-blend Biodegradable PLA cups
"bio-flex"
Play media
Degradation
PLA is degraded abiotically by three mechanisms:[37]
1. Hydrolysis: The ester groups of the main chain are cleaved, thus reducing molecular weight.
2. 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.
3. 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 degradation over a year.[38]
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.[39]
PLA samples of various molecular weights were degraded into methyl lactate (a green solvent) by using
a metal complex catalyst.[40]
PLA 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.[41]
End of life
4 possible end of life scenarios are the most common:
1. 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 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 PLA has SPI
properties (cradle-to-cradle recycling). resin ID code 7
2. Composting: PLA is biodegradable under industrial composting
conditions, starting with chemical hydrolysis process, followed by the
microbial digestion, to ultimately degrade the PLA.
3. Incineration: PLA can be incinerated, leaving no residue and producing 19.5 MJ/kg (8,368
btu/lb) of energy.
4. Landfill: the least preferable option is landfilling because PLA degrades very slowly in
ambient temperatures.
See also
Acrylonitrile butadiene styrene (ABS) - also used for 3D printing
Cellophane, polyglycolide, plastarch material, poly-3-hydroxybutyrate – biologically derived
polymers
Polycaprolactone
Zein, shellac – biologically derived coating materials
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External links
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