Polylactic acid

Polylactic acid or polylactide (PLA) is a thermoplastic aliphatic

Polylactic acid
polyester derived from renewable resources. In 2010, PLA had
the second highest consumption volume of any bioplastic of the
world,[3] although it is still not a commodity polymer. Its
widespread application has been hindered by numerous physical
and processing shortcomings.[4]

The name "polylactic acid" does not comply with IUPAC

standard nomenclature, and is potentially ambiguous or
confusing, because PLA is not a polyacid (polyelectrolyte), but
Identifiers
rather a polyester.[5]
CAS Number 26100-51-6 (http://w
ww.commonchemistr
y.org/ChemicalDetai
Contents l.aspx?ref=26100-51
Production -6)

Materials properties ChemSpider None

Chemical properties Properties
Physical and mechanical properties
Density 1.210–1.430 g·cm
Solvent welding −3[1]
Organic Solvents for PLA
Melting point 150 to 160 °C (302
Applications to 320 °F; 423 to
Degradation 433 K)[1]
End of life Solubility in 0 mg/ml [2]
water
See also
Hazards
References
NFPA 704
External links 1
(fire diamond)
0 0

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]

Physical and mechanical properties

PLA polymers range from amorphous glassy polymer to semi-crystalline and highly crystalline polymer
with a glass transition of 60 °C and melting points of 130-180 °C.[12] PLA has a glass transition
temperature 60–65 °C, a melting temperature 173–178 °C and a tensile modulus 2.7–16 GPa.[13][14]
Heat-resistant PLA can withstand temperatures of 110 °C.[15] The basic mechanical properties of PLA
are between those of polystyrene and PET.[12] 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
later 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,[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]

There is also poly(L-lactide-co-D,L-lactide) (PLDLLA) – used as PLDLLA/TCP scaffolds for bone

engineering.[26][27]

Solvent welding
PLA can be solvent welded using dichloromethane.[28]

Organic Solvents for PLA

PLA is soluble in a range of organic solvents[29]. Ethylacetate, due to its ease of access and low risk of
use, is of most interest. If the filament is soaked in a small amount of ethylacetate, it will dissolve and
can be used to clean 3D printing extruder heads or remove PLA supports. The boiling point of
ethylacetate is low enough to also smooth PLA in a vapor chamber, similar to ABS and acetone. Other
safe solvents to use include propylene carbonate, which is safer than ethylacetate but is difficult to
purchase commercially. Pyridine can also be used however this is less safe than ethylacetate and
propylene carbonate. It also has a distinct bad fish odor.

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

Tea bags made of PLA.

Peppermint tea is enclosed. 3D printing of a microcoil using
a conductive mixture of
polylactide and carbon
nanotubes. [36]
 3D printed human skull with
data from computed
tomography. Transparent PLA.

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
"Your plastic pal" | The Economist (http://www.economist.com/node/14960045)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Polylactic_acid&oldid=929548482"

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