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olylactic acid

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Polylactic acid


CAS Number  26100-51-6

ChemSpider  none

ECHA InfoCard 100.128.355


Density 1.210–1.430 g·cm−3 [1]

Melting point 150 to 160 °C (302 to 320 °F; 423 to

433 K)[1]

Solubility in water Insoluble in water[2]


NFPA 704

Except where otherwise noted, data are given for materials in
their standard state (at 25 °C [77 °F], 100 kPa).

[5] . chips or starch (mostly in Asia). and that is undesirable because water causes chain-transfer leading to low molecular weight material. such as corn starch (in the United States and Canada). Water removal by application of a vacuum or by azeotropic distillation is crucial to favor polycondensation over transesterification. polycondensation is done in the melt or as a solution. The most common route to PLA is the ring-opening polymerization of lactide with various metal catalysts(typically tin octoate) in solution.[5] Another route to PLA is the direct condensation of lactic acid monomers.1Manufacturers  2Chemical and physical properties  3Applications  4Recycling  5Degradation  6See also  7References  8External links Production[edit] Producers have several industrial routes to usable (i. Thereafter. Molecular weights of 130 kDa can be obtained this way. in the melt. lactide. This process needs to be carried out at less than 200 °C. or sugarcane (in the rest of the world). Even higher molecular weights can be attained by carefully crystallizing the crude polymer from the melt. reducing its stereoregularity compared to the starting material (usually corn starch). the entropically favored lactide monomer is generated. Carboxylic acid and alcohol end groups are thus concentrated in the amorphous region of the solid polymer. and so they can react. The direct condensation is thus performed in a stepwise fashion. Two main monomers are used: lactic acid.[3] The name "polylactic acid" does not comply with IUPAC standard nomenclature. cassava roots. because PLA is not a polyacid (polyelectrolyte). high molecular weight) PLA.e. and is potentially ambiguous or confusing. above that temperature. Molecular weights of 128–152 kDa are obtainable thus. The metal-catalyzed reaction tends to cause racemization of the PLA. where short oligomeric units are combined to give a high molecular weight polymer strand. and the cyclic di-ester. where lactic acid is first oligomerized to PLA oligomers.[4] Contents [hide]  1Production o 1. but rather a polyester. PLA had the second highest consumption volume of any bioplastic of the world. or as a suspension. Infobox references Poly(lactic acid) or polylactic acid or polylactide (PLA) is a biodegradable and bioactive thermoplastic aliphatic polyester derived from renewable resources. This reaction generates one equivalent of water for every condensation (esterification) step. In 2010.

(June 2015) (Learn how and when to remove this template message) As of June 2010. Corbion PURAC is a listed company in the Netherlands. NatureWorks was the primary producer of PLA (bioplastic) in the United States.[8][9] Manufacturers[edit] This section does not cite any sources.Polymerization of a racemic mixture of L.000 ton PLA plant in Thailand by 2018.000t. Futerro. because its polymerization is driven by the loss of one equivalent of carbon dioxide per equivalent of lactic acid.500 tonnes/year. and hence many important properties. which is developing a second generation polylactic acid product. The Resomer brand of PDLLA is produced in the Health and Nutrition business segment. and runs about 100°C lower in temperature. This compound is more reactive than lactide. and operating plants worldwide. Corbion PURAC Biomaterials (The Netherlands) who have announced a new 75. Unsourced material may be challenged and removed. This project includes the building of a PLA pilot plant in Belgium capable of producing 1. This condensation reaction is a one-step process. which is amorphous. lactic acid O-carboxyanhydride ("lac-OCA"). Galactic and Total Petrochemicals operate a joint venture. Use of stereospecific catalysts can lead to heterotactic PLA which has been found to show crystallinity. Water is not a co-product.and D-lactides usually leads to the synthesis of poly- DL-lactide (PDLLA). and to a lesser extent on the type of catalyst used.[7] Another method devised is by contacting lactic acid with a zeolite. The degree of crystallinity. Other companies involved in PLA manufacturing are Evonik Industries (Germany). Chemical and physical properties[edit] . produced from the D-isomer of lactid acid. and the only producer of PDLA. a five-membered cyclic compound has been used academically as well.[6] The direct biosynthesis of PLA similar to the poly(hydroxyalkanoate)s has been reported as well. is largely controlled by the ratio of D to L enantiomers used. Apart from lactic acid and lactide. The second biggest producer of PLA in the world is the weforyou Group with an annual capacity of pure PLA and compounds of 50. The primary producer of PDLLA is Evonik Industries and Corbion PURAC. and several[which?] Chinese manufacturers. Please help improve this section by adding citations to reliable sources.

PLLA has a crystallinity of around 37%. thereby increasing the crystallization rate. The temperature stability is maximised when a 1:1 blend is used. PDLA acts as a nucleating agent.[17] 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).[15] It was found to range widely depending on printing conditions.[18][19] Applications[edit] Mulch film made of PLA-blend "bio-flex" Biodegradable PLA cups in use at a restaurant . PDLA and PLLA form a highly regular stereocomplex with increased crystallinity. a glass transition temperature 60–65 °C. there is still a substantial improvement. but even at lower concentrations of 3–10% of PDLA.L-lactide) (PLDLLA) – used as PLDLLA/TCP scaffolds for bone engineering. but has a significantly lower maximum continuous use temperature. a melting temperature 173–178 °C and a tensile modulus 2. hot benzene.L-lactide (also known as L-lactide). tetrahydrofuran. several distinct forms of polylactide exist: poly-L-lactide (PLLA) is the product resulting from polymerization of L. using conventional melt spinning processes) and film. which were obtained using RepRap 3-D printers.[10][11] Heat-resistant PLA can withstand temperatures of 110 °C.[12] PLA is soluble in chlorinated solvents. There is also poly(L-lactide-co-D.[13] Polylactic acid can be processed like most thermoplastics into fiber (for example. Biodegradation of PDLA is slower than for PLA due to the higher crystallinity of PDLA. and dioxane.[16] Results of a recent study gave a printed tensile strength of around 50 MPa and show that the act of 3-D printing PLA affects its properties—they showed a strong relationship between tensile strength and percent crystallinity of a 3-D printed sample and a strong relationship between percent crystallinity and the extruder temperature.7–16 GPa.Due to the chiral nature of lactic acid. PLA has similar mechanical properties to PETE polymer. In the latter case.[14] The tensile strength for 3-D printed PLA was previously determined.

Tea bags made of PLA. because it gradually transfers the load to the body (e. RepRap). rods. then burned out in a furnace. film and sheet casting. injection molding. providing access to a wide range of materials. plates. a type of investment casting. so that the resulting void can be filled with molten metal. Transparent PLA. PLA is used as a feedstock material in desktop fused filament fabrication 3D printers (e.g.[23] Depending on the exact type used. This is known as "lost PLA casting". This gradual degradation is desirable for a support structure. and as a mesh. 3D printing of a microcoil using a conductive mixture of polylactide and carbon nanotubes. 3D Printed Human skull with data from Computed Tomography. Being able to degrade into innocuous lactic acid. pins.g. The strength characteristics of PLA and PLLA implants are well documented.[24] . it breaks down inside the body within 6 months to 2 years. PLA is used as medical implants in the form of anchors. and spinning.[20] PLA can be processed by extrusion such as 3d printing. screws. Peppermint tea is enclosed. the bone) as that area heals.[21][22] PLA printed solids can be encased in plaster-like moulding materials.

[26] Pure PLLA foams undergo selective hydrolysis when placed in an environment of Dulbecco’s modified Eagle's medium (DMEM) supplemented with fetal bovine serum (FBS) (a solution mimicking body fluid).[27] . for example as upholstery. PLA depolymerase. PLA also has many potential uses. awnings. It is useful for producing loose-fill packaging. which is undesirable. such as woven shirts (ironability). allowing it to be used in shrink tunnels. making them useful for low-end packaging applications..[dubious – discuss] Degradation[edit] Amycolatopsis and Saccharotrix are able to degrade PLA. A purified protease from Amycolatopsis sp. disposable garments. injection-molded. In the form of fibers and nonwoven fabrics. Enzymes such as pronase and most effectively proteinase K from Tritirachium album degrade PLA. is the main ingredient in Sculptra. either cast. Pure poly-L-lactic acid (PLLA). compost bags. and diapers.[23] Cups and bags have been made from this material. the SPI resin identification code 7 ("others") is applicable for PLA. or spun. feminine hygiene products. something that was not possible until recently. a PLLA scaffold lost about 20% of its weight. In the form of a film. After 30 days of submersion in DMEM+FBS. the monomer can be used for the manufacturing of virgin PLA with no loss of original properties (cradle-to-cradle recycling).[25] Recycling[edit] PLA has SPIresin ID code 7 Currently. it shrinks upon heating. A stereocomplex of PDLA and PLLA has a higher glass transition temperatures. food packaging. When purified. Unlike mechanical recycling. a long- lasting facial volume enhancer. waste material can hold various contaminants.PLA can also be used as a decomposable packaging material. primarily used for lipoatrophy of cheeks. Progress in biotechnology has resulted in the development of commercial production of the D enantiomer form. In Belgium. lending it more mechanical strength. microwavable trays. hot-fill applications and even engineering plastics (in this case. It has a wide range of applications. Such blends also have good form stability and visual transparency. Polylactic acid can be recycled to monomer by thermal depolymerization or hydrolysis. and disposable tableware. can also degrade PLA. Racemic and regular PLLA has a low glass transition temperature. Galactic started the first pilot unit to chemically recycle PLA (Loopla). the stereocomplex is blended with a rubber-like polymer such as ABS). on the other hand.

the ease with which Polylactic Acid melts allows for some interesting applications in 3D printing (namely “lost PLA casting” .g. polyethylene (PE). bottles. screws.” Polylactic Acid is biodegradable and has characteristics similar to polypropylene (PP). and plates that are expected to biodegrade within 6-12 months).g. by contrast. On the other hand.Everything You Need To Know About Polylactic Acid (PLA) What is PLA. PLA has the second largest production volume of any bioplastic (the most common typically cited as thermoplastic starch). PLA) are known as “bioplastics. PLA constricts under heat and is thereby suitable for use as a shrink wrap material. Most plastics. or polystyrene (PS). and biodegradable medical devices (e. pins. It can be produced from already existing manufacturing equipment (those designed and originally used for petrochemical industry plastics). its low glass transition temperature makes many types of PLA (for example. Plastics that are derived from biomass (e. Additionally. plastic cups) unsuitable to hold hot liquid. rods. are derived from the distillation and polymerization of nonrenewable petroleum reserves. Some of the most common uses include plastic films. For more on medical device prototypes (both biodegradable and permanent) read here. Accordingly. Here is a look at some different PLA products on the market: . This makes it relatively cost efficient to produce. and what is it used for? Polylactic Acid (PLA) is different than most thermoplastic polymers in that it is derived from renewable resources like corn starch or sugar cane. There are a vast array of applications for Polylactic more below).

com PLA medical screws. as a plastic electronics part). The huge benefit of PLA as a bioplastic is its versatility and the fact that it naturally degrades when exposed to the environment.g. Accordingly. PLA printing filament. Regular PLLA (Poly-L-lactic Acid). PLA production is a popular idea as it represents the fulfillment of the dream of cost-efficient. For example. non-petroleum plastic production. photo courtesy of DSM. PLA is extremely robust in any normal application (e. there is a high potential for PLA to be very useful in short lifespan applications where biodegradability is highly beneficial ( What Are The Different Types of Polylactic Acid and Why is it Used so Often? There are several different types of Polylactic Acid to include Racemic PLLA (Poly-L-lactic Acid). despite its ability to degrade when exposed to the elements over a long time. as a plastic water bottle or as a container for fruit and vegetables). Of note. PDLA (Poly-D-lactic Acid). photo courtesy Alibaba. They each have slightly different characteristics but are similar in that they are produced from a renewable resource (lactic acid: C3H6O3) as opposed to traditional plastics which are derived from nonrenewable petroleum. and PDLLA (Poly-DL-lactic Acid). PLA for Prototype Development on CNC Machines and 3D Printers: . Compared to conventional plastics (which in the same environment can take several hundred to a thousand years to degrade) this is truly phenomenal. a PLA bottle left in the ocean would typically degrade in six to 24 months.g.

The PLA is later burned out as it has a lower melting temperature than the surrounding material. typically available as a thin film for thermoforming or in the form of plastic pellets for injection molding. which allows them to be . PLA filament for 3D printing is typically available in a myriad of colors. cooled. Instead of burning. PLA is classified as a “thermoplastic” polyester (as opposed to “thermoset”). thermoplastics like Polylactic Acid liquefy. plastic injection mold pellets are typically produced and/or blended together. How is PLA made? Polylactic Acid is principally made through two different processes: condensation and polymerization.PLA is one of two common plastics used on FDM machines (3D printing) and is commonly available as a 3D printable filament. What are the Characteristics of Polylactic Acid? Now that we know what it is used for. Thermoplastic materials become liquid at their melting point (150-160 degrees Celsius in the case of PLA). The condensation process is similar with the principal difference being the temperature during the procedure and the by-products (condensates) that are released as a consequence of the reaction. let’s examine some of the key properties of Polylactic Acid. The most common polymerization technique is known as ring-opening polymerization. One of the interesting things you can do with PLA on a 3D printer is called “lost PLA casting. and reheated again without significant degradation. A major useful attribute about thermoplastics is that they can be heated to their melting point. Polylactic Acid could be CNC machined but it is typically not available in sheet stock or rod form.” This is a process where PLA is printed in the shape of an interior cavity and then encased with plaster-like materials. This is a process that utilizes metal catalysts in combination with lactide to create the larger PLA molecules. the other common 3D printer plastic is ABS. however. and the name has to do with the way the plastic responds to heat. It is. To adjust material properties. The end result is a void that can be filled (often with molten metal).

Is PLA toxic? In solid form. Sounds . You can read about the results here. cane sugar. Even things like a hot car in the summer could cause parts to soften and deform. What are the Disadvantages of Polylactic Acid? PLA has a relatively low glass transition temperature (typically between 111 and 145 °F). We believe that Compostable Bioplastics. we understand the many problems associated with petroleum-based plastics. In fact. deli and takeout containers. are the solution to many of these problems. For a full comparison of the two plastics as they relate to 3D printing read here. and fresh produce packaging. Be careful and closely follow handling instructions for molten polymer in particular. no. typically made from plant matter like vegetable starch. thermoset plastics can only be heated once (typically during the injection molding process). Polylactic Acid (PLA) is a bioplastic generally derived from animal-feed corn that can be used for a myriad of different purposes including cold drink cups. This characteristic makes thermoset materials poor candidates for recycling. during manufacturing processes). Polylactic Acid is a little bit more brittle than ABS for 3D prototyping but it has some advantages as well. What are the properties of PLA? Here at Biomass. The first heating causes thermoset materials to set (similar to a 2-part epoxy) resulting in a chemical change that cannot be reversed. It is often used in food handling and medical implants that biodegrade within the body over time.e. If you tried to heat a thermoset plastic to a high temperature a second time it would simply burn. Like most plastics. it has the potential to be toxic if inhaled and/or absorbed into the skin or eyes as a vapor or liquid (i. By contrast. PLA falls under the SPI resin identification code of 7 ("others").easily injection molded and then subsequently recycled. cellulose (wood fibers) and lactic acid. Polylactic Acid (PLA) is biodegradable. This makes it fairly unsuitable for high temperature applications. Recently researchers from the Illinois Institute of Technology published a paper on Ultrafine Particle (UFP) emissions from commercially available 3D printers using ABS and PLA feedstock.

is based on a resource that can be renewed yearly. right? It is. Conclusion . however. we believe that the infrastructure for commercial composting will follow. PLA can break down into natural elements in less than a month given the right circumstances. Long term plans in the industry include determining effective ways to create PLA plastics from agricultural waste like stalks and stems which could result in bioplastics made from products that are not fit for consumption. there are a limited number of such facilities in the United States which means that it can be difficult to properly dispose of these products. However. Cons of Polylactic Acid (PLA) or “Corn Plastics” PLA Production Depends on Large Fields of Crops While the corn used to create PLA is a renewable resource. PLA Plastics Are Only Compostable in a Commercial Composting Facility Unfortunately. at least in theory. the oil will run out. Today we’ll be looking at a few of the pros and cons of these “corn plastics. however. Eventually. we’ve been warned of the dangerous chemicals that can be released when traditional plastics are incinerated. this can cause problems in the recycling process if the products are not properly sorted before recycling begins. At this time. many people point out that the fields use to grow these crops could be used to create foodstuffs for the world’s growing population. Improperly Disposed PLA Plastics Can Contaminate Recycling Processes Whether or not commercial composting facilities are locally available. PLA.” Pros of Polylactic Acid (PLA) or “Corn Plastics” PLA is Derived From a Renewable Resource One of the major problems with petroleum-based plastics is that they are derived from oil which is only available in finite amounts throughout the world. as the industry grows.great. these products need to be sent to a commercial composting facility for processing. most PLA plastic will not break down into natural elements in your backyard composting pile. They do have a point. Instead. Being biologically based. In practice. being derived from corn. This is especially true when these products end up in landfills where sunlight and air exposure are drastically curtailed. Because they are derived from very different elements. On the other hand. PLA Does Not Produce Toxic Fumes If Incinerated For decades. PLA Plastics Are Compostable It is estimated that traditional plastics can take centuries to break down and may never break down into natural elements. but it is important to remember that the bioplastics industry is still young. things are a little more complicated. PLA plastics do not produce these toxic fumes if they end up being incinerated instead of finding their way to a commercial composting facility. many PLA products end up getting mixed in with traditionally recyclable plastics.

To that end. But as long as we live in a society that embraces disposable plastic containers. And that points to another problem: There are currently a few hundred industrial- grade composting facilities across the United States. Ireland. MOST PLA USES GENETICALLY MODIFIED CORN Another downside of PLA is that it is typically made from genetically modified corn. The largest producer of PLA in the world is NatureWorks.It’s not surprising that these pros and cons prove that PLA plastics are not a perfect solution. PLA is poised to play a big role as a viable. PLA HELPS TO REDUCE GREENHOUSE GAS EMISSIONS Proponents also tout the use of PLA—which is technically “carbon neutral” in that it comes from renewable. RECYCLERS CAN’T MIX PLA AND OTHER PLASTICS Another issue with PLA is that. or in a landfill packed so tightly that no light and little oxygen are available to assist in the process. an industrial composting facility heated to 140 degrees Fahrenheit and fed a steady diet of digestive microbes. not a recycling facility. PLA needs to head to a composting facility. it must be kept separate when recycled. PLA BIODEGRADES SLOWLY UNLESS SUBJECTED TO INDUSTRIAL COMPOSTING But critics say that PLA is far from a panacea for dealing with the world’s plastic waste problem. But it will take far longer in a compost bin. Indeed. a subsidiary of Cargill.000 years to decompose in a landfill. According to Elizabeth Royte. a plastic substitute made from fermented plant starch (usually corn) is quickly becoming a popular alternative to traditional petroleum-based plastics. Uganda and San Francisco in banning plastic grocery bags responsible for so much so-called “white pollution” around the world. at least in the United States. PLA may well break down into its constituent parts (carbon dioxide and water) within three months in a “controlled composting environment. But the future costs of genetic .” that is. Being plant-based. although PLA does biodegrade. With increasing demand for corn to make ethanol fuel. PLA also will not emit toxic fumes when incinerated. when it has out served its usefulness. South Africa. Polylactic acid (PLA). For one thing. we think that products made from PLA are a positive step toward a world less dependent on oil and more focused on renewable solutions. it does so very slowly. it’s no wonder that Cargill and others have been tampering with genes to produce higher yields. writing in Smithsonian. biodegradable replacement. because it is of different origin than regular plastic. lest it contaminate the recycling stream. which is the world’s largest provider of genetically modified corn seed. analysts estimate that a PLA bottle could take anywhere from 100 to 1. let alone PLA. As more and more countries and states follow the lead of China. carbon-absorbing plants—as yet another way to reduce our emissions of greenhouse gases in a quickly warming world. we need to be working toward finding solutions that are less harmful to the environment than traditional plastics.

PLA may not be much better than the plain old plastic it’s designed to make obsolete. PLA HAS MANY USES As for other types of PLA items—such as those plastic “clamshells” that hold cut fruit (and there is a whole host of industrial and medical products now made from PLA)—there is no reason to pass them by. But until the kinks are worked out on the disposal and reprocessing end.modification (and the associated pesticides) to the environment and human health are still largely unknown. baskets and backpacks for grocery shopping (most chains now sell canvas bags for less than a dollar apiece) to safe. GREEN-MINDED CONSUMERS MAY PREFER ALTERNATIVES TO PLASTICS While PLA has promise as an alternative to conventional plastic once the means of disposal are worked out. . consumers might be better served by simply switching to reusable containers—from cloth bags. reusable (non-plastic) bottles for beverages. DESPITE PROBLEMS.