Biodegradable

polymer

Example of cutlery made from biodegradable

plastic

Biodegradable polymers are a special

class of polymer that breaks down after
its intended purpose by bacterial
decomposition process to result in
natural byproducts such as gases (CO2,
N2), water, biomass, and inorganic
salts.[1][2] These polymers are found both
naturally and synthetically made, and
largely consist of ester, amide, and ether
functional groups. Their properties and
breakdown mechanism are determined
by their exact structure. These polymers
are often synthesized by condensation
reactions, ring opening polymerization,
and metal catalysts. There are vast
examples and applications of
biodegradable polymers.

Bio-based packaging materials have

been introduced as a green alternative in
the past decades, among which, edible
films have gained more attention due to
their environmentally-friendly
characteristics, vast variety and
availability, non-toxicity, and low cost.[3]

History
Biodegradable polymers have a long
history, and since many are natural
products, the precise timeline of their
discovery and use cannot be accurately
traced. One of the first medicinal uses of
a biodegradable polymer was the catgut
suture, which dates back to at least 100
AD.[4] The first catgut sutures were made
from the intestines of sheep, but modern
catgut sutures are made from purified
collagen extracted from the small
intestines of cattle, sheep, or goats.[5]

The concept of synthetic biodegradable

plastics and polymers was first
introduced in the 1980s.[6] In 1992, an
international meeting was called where
leaders in biodegradable polymers met to
discuss a definition, standard, and
testing protocol for biodegradable
polymers.[2] Also, oversight organizations
such as American Society for Testing of
Materials (ASTM) and the International
Standards Organization (ISO) were
created.[7] Large clothing and grocery
store chains have pushed to utilize
biodegradable bags in the late 2010s.
Biodegradable polymers also received
notice from various fields in 2012 when
Professor Geoffrey Coates of Cornell
University received the Presidential Green
Chemistry Challenge Award. As of 2013,
5-10% of the plastic market focused on
biodegradable polymer derived
plastics.[8]

Structure and properties

The structure of biodegradable polymers
is instrumental in their properties. While
there are innumerable biodegradable
polymers, both synthetic and natural,
there are a few commonalities among
them.
Structure

Biodegradable polymers tend to consist

of ester, amide, or ether bonds. In
general, biodegradable polymers can be
grouped into two large groups based on
their structure and synthesis. One of
these groups is agro-polymers, or those
derived from biomass.[1] The other
consists of biopolyesters, which are
those derived from microorganisms or
synthetically made from either naturally
or synthetic monomers.
Biodegradable polymers organization based on
structure and occurrence[1]

Agro-polymers include polysaccharides,

like starches found in potatoes or wood,
and proteins, such as animal based whey
or plant derived gluten.[1] Polysacharides
consist of glycosidic bonds, which take a
hemiacetal of a saccharide and binds it
to a alcohol via loss of water. Proteins
are made from amino acids, which
contain various functional groups.[9]
These amino acids come together again
through condensation reactions to form
peptide bonds, which consist of amide
functional groups.[9] Examples of
biopolyesters include
polyhydroxybutyrate and polylactic
acid.[1]

Properties

Even though biodegradable polymers

have numerous applications, there are
properties that tend to be common
among them. All biodegradable polymers
should be stable and durable enough for
use in their particular application, but
upon disposal they should easily break
down.[7] Polymers, specifically
biodegradable polymers, have extremely
strong carbon backbones that are
difficult to break, such that degradation
often starts from the end-groups. Since
the degradation begins at the end, a high
surface area is common as it allows easy
access for either the chemical, light, or
organism.[2] Biodegradable polymers
also tend to have minimal chain
branching as this cross linking often
decreases the number of end groups per
unit weight. Crystallinity is often low as it
also inhibits access to end groups.[8] A
low degree of polymerization is normally
seen, as hinted at above, as doing so
allows for more accessible end groups
for reaction with the degradation initiator.
Another commonality of these polymers
is their hydrophillicity.[2] Hydrophobic
polymers and end groups will prevent an
enzyme from easily interacting if the
water-soluble enzyme cannot easily get
in contact with the polymer.

Other properties of biodegradable

polymers that are common among those
used for medicinal usages include being:

non-toxic
 capable of maintaining good
mechanical integrity until degraded
capable of controlled rates of
degradation[10]

A goal is not to elicit the immune

response, and the products of
degradation also need not to be toxic.
These are important as biodegradable
polymers are used for drug delivery
where it is critical to slowly release the
drug into the body over time instead of all
at once and that the pill is stable in the
bottle until ready to be taken.[10] Factors
controlling the rate of degradation
include percent crystallinity, molecular
weight, and hydrophobicity. The
degradation rate depends on the location
in the body, which influences the
environment surrounding the polymer
such as pH, enzymes concentration, and
amount of water, among others. These
are rapidly decomposed.[10]

Synthesis
One of the most important and most
studied groups of biodegradable
polymers are polyesters. Polyesters can
be synthesized in a number of ways
including direct condensation of alcohols
and acids, ring opening polymerizations
(ROP), and metal-catalyzed
polymerization reactions.[11] A great
disadvantage of the step-wise
polymerization via condensation of an
acid and an alcohol is the need to
continuously remove water from this
system in order to drive the equilibrium
of the reaction forward.[12] This can
necessitate harsh reaction conditions
and long reaction times, resulting in a
wide dispersity. A wide variety of starting
materials can be used to synthesize
polyesters, and each monomer type
endows the final polymer chain with
different characteristics and properties.
The ROP of cyclic dimeric glycolic or
lactic acid forms α-hydroxy acids which
then polymerize into poly-(α-esters).[12] A
variety of organometallic initiators can be
used to start the polymerization of
polyesters, including tin, zinc, and
aluminum complexes. The most
common is tin(II)octanoate and has been
approved as a food additive by the U.S.
FDA, but there are still concerns about
using the tin catalysts in the synthesis of
biodegradable polymers for biomedical
uses.[11] The synthesis of poly(β-esters)
and poly(γ-esters) can be carried out by
similar ROP or condensation methods as
with poly(γ-esters). Development of
metal-free process that involve the use of
bacterial or enzymatic catalysis in
polyester formation is also being
explored.[13][14] These reactions have the
benefit of generally being regioselective
and stereospecific but suffer from the
high cost of bacteria and enzymes, long
reaction times, and products of low
molecular weight.

Example of routes to polyester formation using

lactic acid. a) Condensation of lactic acid into
dimeric lactide followed by ring-opening
polymerization of to form poly(lactic acid); b) Direct
condensation of lactic acid, demonstrating the
need to continuously remove water from the
system in order to drive the reaction forward.[15]
While polyesters dominate both the
research and industrial focus on
synthetic biodegradable polymers, other
classes of polymers are also of interest.
Polyanhydrides are an active area of
research in drug delivery because they
only degrade from the surface and so are
able to release the drug they carry at a
constant rate.[11] Polyanhydrides can be
made via a variety of methods also used
in the synthesis of other polymers,
including condensation,
dehydrochlorination, dehydrative
coupling, and ROP. Polyurethanes and
poly(ester amide)s are used in
biomaterials.[16] Polyurethanes were
initially used for their biocompatibility,
durability, resilience, but are more
recently being investigated for their
biodegradability. Polyurethanes are
typically synthesized using a
diisocyanate, a diol, and a polymer chain
extender.[11] The initial reaction is carried
out between the diisocyanate and the
diol, with the diisocyanate in excess to
ensure that the ends of the new polymer
chain are isocyanate groups. This
polymer can then be reacted with either a
diol or a diamine to form urethane or
urethane-urea end groups, respectively.
The choice of terminal groups affects the
properties of the resulting polymer.
Additionally, the use of vegetable oil and
biomass in the formation of
polyurethanes, as well as the conversion
of polyurethanes to polyols, is an active
area of research.[17]

Synthesis of polyurethane from a diisocyanate and

a diol. To cap this polymer, chain extenders of
either diols or diamines can be added in order to
tailor the properties.

The mechanical properties of

biodegradable polymers can be
enhanced with the addition of fillers or
other polymers to make a composite,
blend, or copolymer. Some fillers are
natural fiber reinforcements such as silk
nanofibers, bamboo, jute, in addition to
nano-clay, and carbon nanotubes as
alternatives to name a few.[18][19] Each of
these enhancements have a unique
property that not only improve strength,
but also processability, through humidity
resistance, reduced gas permeability, and
have shape memory/recovery. Some
examples, such as the
polyhydroxyalkanoates/polylactic acid
blend, shows an exceptional increase in
the toughness without sacrificing optical
clarity, and the copolymer poly(L-lactide-
co-ε-caprolactone) has shown shape
memory behavior depending on the
concentration of poly-ε-caprolactone
added.[20][21]
Mechanism of breakdown
In general, biodegradable polymers break
down to form gases, salts, and
biomass.[22] Complete biodegradation is
said to occur when there are no
oligomers or monomers left.[22] The
breakdown of these polymers depend on
a variety of factors including the polymer
and also, the environment the polymer is
in. Polymer properties that influence
degradation are bond type, solubility, and
copolymers among others.[2] The
surrounding environment of the polymer
is just as important as the polymer
structure itself. These factors included
items such as the pH, temperature,
micoorganisms present, and water are
just a few examples.[1]

There are two primary mechanisms

through which biodegradation can occur.
One is through physical decomposition
through reactions such as hydrolysis and
photodegradation, which can lead to
partial or complete degradation.[7] The
second mechanistic route is through
biological processes which can be
further broken down into aerobic and
anaerobic processes.[2] The first involves
aerobic biodegradition, where oxygen is
present and important. In this case, the
general equation seen below where
Cresidue represents smaller fragments of
the initial polymer such as oligomers.

General equation for aerobic biodegradition[2]

The second mechanism of

biodegradation is by anaerobic
processes, where oxygen is not present.

General equation for anaerobic biodegradition[2]

There are numerous organisms that have

the ability to break down natural
polymers.[2] There are also synthetic
polymers that have only been around for
a hundred years with new features that
microorganisms do not have the
capability to break down. It will take
millions of years before organisms can
adapt to degrade all of these new
synthetic polymers. Typically, after
physical processes carry out the initial
breakdown of the polymer,
microorganisms will then take what is
left and break down the components into
even simpler units.[2] These
microorganisms normally take polymer
fragments, such as oligomers or
monomers, into the cell where enzymes
work to make adenosine triphosphate
(ATP) and polymer end products carbon
dioxide, nitrogen gas, methane, water,
minerals, and biomass.[2] These enzymes
act in a variety of ways to break down
polymers including through oxidation or
hydrolysis. Examples of key enzymes
include proteases, esterases,
glycosidases, and manganese
peroxidases.

Applications and uses

Biodegradable polymers are of
significant interest to a variety of fields
including medicine, agriculture, and
packaging. One of the most active areas
of research in biodegradable polymer is
in controlled drug delivery and release.

Medical

Biodegradable polymers have an

innumerable uses in the biomedical field,
particularly in the fields of tissue
engineering and drug delivery.[11][23] In
order for a biodegradable polymer to be
used as a therapeutic, it must meet
several criteria: 1) be non-toxic in order to
eliminate foreign body response; 2) the
time it takes for the polymer to degrade
is proportional to the time required for
therapy; 3) the products resulting from
biodegredation are not cytotoxic and are
readily eliminated from the body; 4) the
material must be easily processed in
order to tailor the mechanical properties
for the required task; 5) be easily
sterilized; and 6) have acceptable shelf
life.[6][24]

Biodegradable polymers are of great

interest in the field of drug delivery and
nanomedicine. The great benefit of a
biodegradable drug delivery system is
the ability of the drug carrier to target the
release of its payload to a specific site in
the body and then degrade into nontoxic
materials that are then eliminated from
the body via natural metabolic
pathways.[25] The polymer slowly
degrades into smaller fragments,
releasing a natural product, and there is
controlled ability to release a drug. The
drug slowly releases as polymer
degrades. For example, polylactic acid,
poly(lactic-co-glycolic) acid, and
poly(caprolactone), all of which are
biodegradable, have been used to carry
anti-cancer drugs. Encapsulating the
therapeutic in a polymer and adding
targeting agents decreases the toxicity of
the drug to healthy cells.
Sutures made from polyglycolic acid. These sutures
are absorbable and will be degraded by the body
over time.

Biodegradable polymers and

biomaterials are also of significant
interest for tissue engineering and
regeneration. Tissue engineering is the
ability to regenerate tissue with the help
of artificial materials. The perfection of
such systems can be used to grow
tissues and cells in vitro or use a
biodegradable scaffold to construct new
structures and organs in vitro.[26] For
these uses, a biodegradable scaffold is
obviously preferred as it reduces the risk
of immunological reaction and rejection
of the foreign object. While many of the
more advanced systems are not ready
for human therapeutics, there is
significant positive research in animal
studies. For example, it was possible to
successfully grow rat smooth muscle
tissue on a polycaprolactone/polylactide
scaffold.[27] Further research and
development may allow for this
technology to be used for tissue
replacement, support, or enhancement in
humans. One of the ultimate goals of
tissue engineering is the creation of
organs, such as the kidney, from basic
constituents. A scaffolding is necessary
to grow the entity into a functioning
organ, after which the polymer scaffold
would degrade and be safely eliminated
from the body. There are reports of using
polyglycolic acid and polylactic acid to
engineer vascular tissue for heart
repair.[28] The scaffold can be used to
help create undamaged arteries and
vessels.

In addition to tissue engineering,

biodegradable polymers are being used
orthopedic applications, such as bone
and joint replacement.[29] A wide variety
of non-biodegradable polymers have
been used for orthopedic applications
including silicone rubber, polyethylene,
acrylic resins, polyurethane,
polypropylene, and
polymethylmethacrylate. The primary
role of many of these polymers was to
act as a biocompatible cement in the
fixation of prostheses and in the
replacement of joints. Newer biologically
compatible synthetic and natural
biodegradable polymers have been
developed; these include polyglycolide,
polylactide, polyhydroxobutyrate,
chitosan, hyaluronic acid, and hydrogels.
In particular, poly(2-hydroxyethyl-
methacrylate), poly(ethylene glycol),
chitosan, and hyaluronic acid have been
used extensively in the repair of cartilage,
ligaments, and tendons. For example,
poly(L-lactide) (PLA), is used to make
screws and darts for meniscal repair and
is marketed under the trade name
Clearfix Mensical Dart/Screw.[24] PLA is a
slow degrading polymer and requires
times greater than two years to degrade
and be absorbed by the body.

Packaging and materials

A trash bag made of a poly(lactic acid) blend,

marketed under the brand Bio-Flex® [30]
In addition to medicine, biodegradable
polymers are often used to reduce the
volume of waste in packaging
materials.[6] There is also significant
effort to replace materials derived from
petrochemicals with those that can be
made from biodegradable components.
One of the most commonly used
polymers for packaging purposes is
polylactic acid, PLA.[31] The production of
PLA has several advantages, the most
important of which is the ability to tailor
the physical properties of the polymer
through processing methods. PLA is
used for a variety of films, wrappings,
and containers (including bottles and
cups). In 2002, FDA ruled that PLA was
safe to use in all food packaging.[32]
BASF markets a product called ecovio®
which is a biobased blend of the
company's certified compostable and
biodegradable co-polyester ecoflex® and
PLA.[33] An application for this certified
compostable and bio-based material is
for any kind of plastic films such as
shopping bags or organic waste bags.
ecovio® can also be used in other
applications, like thermoformed and
injection moulded articles. Even paper-
coating or particle foamed products can
be produced by this very versatile
biopolymer.

Notable examples
2012 Presidential Green
Chemistry Challenge

Carbon dioxide directly used in a polymer backbone

Each year hundreds of millions of tons of

plastics are produced from petroleum.[34]
Most of these plastics will remain in
landfills for years to come or litter the
environment posing significant health
risks to animals; however, the average
person's lifestyle would be impractical
without them (see Applications). One
solution to this conundrum lies in
biodegradable polymers. These polymers
have the distinct advantage that over
time they will break down. Dr. Geoffrey
Coates headed research to create
catalysts that can not only efficiently
create these biodegradable polymers, but
the polymers also incorporate the
greenhouse gas and global warming
contributor, CO2, and, environmentally
present ground-ozone producer, CO.[35]
These two gases can be found or
produced in high concentrations from
agricultural waste, coal, and industrial
applications as byproducts.[36] Not only
do the catalysts utilize these normally
wasted and environmentally unfriendly
gases, but they also do it extremely
efficiently with high turnover numbers
and frequencies in addition to good
selectivity.[36] These catalysts have been
actively used by Novomer Inc to make
polycarbonates that can replace the
current coating bisphenol A (BPA) found
in many food and drink packaging.
Novomer's analysis shows that if used in
all cases, these biodegradable polymer
coatings could not only sequester, but
also avoid further production of CO2 in
hundreds of millions of metric tons in
just a single year.[36]

Future concerns and

potential problems
First, the properties such as weight
capacity of biodegradable polymer are
different from the traditional polymer,
which may be unfavorable in many daily
applications. Second, engineering issues.
Biodegradable polymers are mostly
plant-base materials, which means they
are originally come from organic source
like soybean or corn. These organic
plants have the chance to be sprayed
with pesticides which contain chemicals
which can contaminate the crops and be
transferred into the final finished product.
Third, low biodegradation rate. Compared
to the traditional deposition way, the
biodegradation for polymer has a longer
degradation period. Take
Polyhydroxyalkanoates(PHAs) as an
example, PHAs have a degradation
period for up to three to six months. Last,
the cost issue. The production
technology of biodegradable polymer is
still immature, the cost of resources such
as labor and raw materials in large
production quantity scale will be
comparable high.

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External links
Polyketals - esciencenews.com
"New emerging trends in synthetic
biodegradable polymers – Polylactide:
 A critique." European Polymer Journal,
2007, 43 4053-4074

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