Polyurethanes in Biomedical Engineering
Chemistry and Synthesis of Polyurethanes
Thermoplastic polyurethanes are a class of linear
segmented copolymers that have excellent mechanical
properties and relatively good biostability. These
elastomers characteristically have high-tensile strength
and elongation, excellent tear strength, and good
abrasion resistance. Their chemical makeup offers
substantial opportunities to tailor structure to meet
specific property requirements. They are easily pro-
cessed using both common melt-processing techniques
and solution processing. This enables fabrication of a
variety of medical implants. The nearest competitor to
polyurethane elastomers in biomedical applications is
silicone rubber. Although silicone rubber has excellent
biocompatibility, the inherently low tensile strength,
poor abrasion, and tear resistance, as well as some
limitations in processing, restrict its use in medical
implants.
The use of polyurethanes for medical implants was
first suggested by Boretos and Pierce in 1967. Since
then, polyurethanes have been recognized as suitable
for the construction of a variety of medical devices
such as those listed in Table 1.
Polyurethanes used in early implant applications
were those developed for nonmedical applications.
However, since the mid-1980s, several research groups
have focused on the development of chemistries that
achieve a combination of good mechanical properties,
processability, biocompatibility, and resistance to
degradation. This article outlines polyurethane chem-
istry and synthesis, properties, processing, and mor-
phology. Recent advances in design and synthesis of
new polyurethanes will be reviewed with mention
of test methods for screening polyurethanes for
suitability.
Table 1
Applications of polyurethanes.
Blood bags, closures, fittings
Blood oxygenating tubing, conduits
Cardiac assist pump bladders, tubing, housing, coatings
Catheters
Dental cavity liners
Endotracheal tubes
Heart pacemaker connectors, coatings, lead insulators,
fixation devices
Hemodialysis tubing, membranes, connectors
Heart valves
Orthopedic splints, bone adhesives
Percutaneous shunts
Reconstructive surgery materials
Skin dressings and tapes
Surgical drapes
Suture material
Synthetic bile ducts
Transdermal drug delivery patches
Vascular grafts and patches
Wound dressings
1.
Thermoplastic polyurethane elastomers are charac-
terized by the presence of urethane (carbamate) groups
(1)
1
They are prepared from three components—a di-
isocyanate, a macrodiol, and a chain extender. The
reactions involved are illustrated in Scheme 1.
Although there are many potential combinations of
diisocyanates, macrodiols, and chain extenders rela-
tively few have been used for medical applications.
Owing to the ease of handling, symmetric structure,
and high reactivity, 4,4h-methylenediphenyl di-
isocyanate (MDI) (2) is the most frequently used
diisocyanate as it provides good properties. Ali-
phatic diisocyanates, such as hydrogenated MDI and
trans-cyclohexane-1,4-diisocyanate have been used
occasionally (Lamba et al. 1998, Szycher 1999).
2
The chain extender is usually a low molecular weight
( 400) diol such as 1,4-butanediol (3), although
low molecular weight diamines, such as ethylene
diamine can be used. Chain extension with diols
usually affords thermally processable materials, while
diamines give polyurethane-ureas that are generally
only suitable for solvent casting. The macrodiol is
a diol of higher molecular weight (400–2000). Until
recently, most medical grade polyurethanes were
prepared from poly(tetramethylene oxide) (PTMO)
(4) macrodiol.
3
n
4
Although the main reaction involved in poly-
urethane synthesis is the formation of carbamate
(urethane) linkages by the reaction of isocyanates and
alcohols, the polymerization is sometimes complicated
by other side reactions (Oertel 1985, Wirpsza 1993).
These include allophanate formation via reaction of
an isocyanate group with urethane N–H bonds, and in
case of ureas (when the chain extender is a diamine or
water) the formation of biuret linkages. A further
complication may arise from the trimerization of
1
Polyurethanes in Biomedical Engineering
Scheme 1
isocyanate groups to form isocyanurates. These side
reactions generally lead to branching and cross-
linking. A low level of cross-linking, particularly by
allophanates, is sometimes introduced to the poly-
urethane by adjustment of reactant stoichiometry to
improve mechanical properties. This strategy for
introducing low levels of cross-linking has the ad-
vantage over, say those involving the use of tri-
functional chain extenders, in that it can lead to
thermally processable products, since the reactions
that lead to allophanates are thermally reversible.
Purity of reagents and prevention of exposure to
moisture are of crucial importance to achieve high
molecular weight polyurethanes.
Polyurethanes can be prepared via one- or two-step
batch procedures or by semicontinuous processes
such as reactive extrusion (Oertel 1985, Wirpsza 1993).
One-step batch synthesis involves reacting a mixture
of the predried macrodiol and the chain extender with
the diisocyanate. The reaction is generally catalyzed
with dibutyltin dilaurate, stannous octoate or amine
catalysts and is exothermic. The mixing of reagents is
typically carried out between 70 mC and 80 mC. This
one-step reaction can also be carried out in special
continuous mixing machines, reactive extruders, or in
continuous injection molding machines. For large-
scale industrial production two methods are used
commonly: the belt process and reactive extrusion. In
the belt process, after the ingredients are mixed, they
are poured onto a belt for curing. The slab is then
granulated, and pelletized using an extruder to obtain
uniform pellets. In the case of reactive extrusion, the
polymerization is almost complete at the end of
extrusion and uniform pellets can be formed directly
from the melt. Relatively small continuous molding or
casting machines, such as those made by Spritztechnik,
are capable of outputs of 1–2 kg minV".
2
The two-step procedure gives improved control of
polymer architecture and can be carried out in bulk or
in solvents, such as rigorously dried N,N-dimethyl-
formamide or N,N-dimethylacetamide. Polymeriza-
tions carried out in solvent are commercially less
attractive and generally reserved for the preparation
of solvent-castable polyurethanes or for laboratory
investigations. The two-step batch procedure involves
end-capping the macrodiol with diisocyanate and
subsequently chain extending the resulting prepolymer
with a low molecular weight diol or diamine. Both
bulk and solution two-step processes are useful
methods for preparing polyurethanes from nonpolar
macrodiols, which are less compatible with the gen-
erally more polar hard segment precursors. End-
capping in the first step changes the solubility par-
ameter of the macrodiol making it more compatible
with other components and preventing a com-
positionally heterogeneous polymerization.
2. Properties and Morphology
The good mechanical properties of polyurethanes are
the result of a two-phase morphology (Lamba et al.
1998, Szycher 1999). The chemical structures of the
components, relative amount of soft and hard seg-
ment, method of synthesis, and processing conditions
influence morphology. One phase is derived from the
macrodiol and is generally referred to as the soft
domain since it imparts softness and extensibility. It is
relatively immiscible with the other phase, referred to
as the hard phase, which is derived from the diiso-
cyanate and chain extender. The two phases can
associate through hydrogen bonding, particularly
when the macrodiol is a polyester, polycarbonate, or
polyether. The hard phase provides cohesive strength
to the polymer matrix. The hard phase is dispersed

within the continuous soft phase and its cohesion is
assisted by H-bonding of the urethane groups and, in
the case of aromatic diisocyanates, by pi-electron
association.
At moderate extension (e.g., 250%), macrodiol
chains in the soft phase become aligned and may
stress-crystallize. At higher extension, further crystal-
lization occurs. The ability to stress-crystallize
depends on the type of macrodiol as well as its
molecular weight. Typically polyether macrodiols
such as PTMO exhibits this behavior. Stress crystal-
lization improves mechanical properties.
Differential scanning calorimetry (DSC) is widely
used for the determination of molecular organization,
including phase segregation, glass transition, and
melting of crystalline regions. Typical polyurethane
transitions include glass transition of soft and hard
domains, sometimes an amorphous interfacial zone, a
short-range order melting endotherm of the hard
phase attributable to annealing effects, and endo-
therms associated with long-range order of crystalline
portions of either soft or hard segments. The extent of
phase mixing is reflected in the temperature shifts
observed relative to the transition temperatures of the
respective pure segments. For example, a higher soft-
segment glass transition temperature compared to
that of the pure soft segment indicates an increased
presence of hard segments dissolved in the soft
domains.
DMTA (dynamic mechanical thermal analysis) is a
popular method for measuring thermomechanical
properties of polyurethanes. The glass transition
temperature is easily measured by this technique
which involves the application of a sinusoidal load
on the sample. DMTA readily detects changes in
internal molecular mobility and is helpful in probing
phase structure and morphology.
For more detailed morphology characterization,
techniques such as wide and small angle x ray
scattering (WAXS and SAXS, respectively) are used.
WAXS can be used to determine crystallinity and
paracrystallinity order, whereas SAXS can provide
information on domain sizes and spacing, the relative
degree of phase separation and domain purity, and the
thickness of the interface between the soft and hard
segment domains.
Because of interchain hydrogen bonding, the mech-
anical properties of polyurethanes are less influenced
by polymer molecular weight than are nonpolar
polymers such as polyethylene. Thus, elastomers of
Mn " 50 000, or even 25 000, can still have good
properties, although higher molecular weight
materials (
75 000) are preferred.
3. Processing
Polyurethane elastomers can be processed using such
techniques as extrusion, compression molding, and
injection molding (Oertel 1985). Solvent casting is also
Polyurethanes in Biomedical Engineering
a widely used fabrication method, and the most
commonly used solvent is N,Nh-dimethylacetamide.
Since most polyurethane elastomers absorb moisture,
proper drying is a critical first step in polyurethane
processing. Moisture can result in significant degra-
dation at processing temperatures causing voids and
other defects in molded and extruded parts. Typically,
polyurethanes are dried at 105 mC for 2 h in a tray or a
dehumidifying hopper-drier before processing, but the
conditions have to be optimized depending on initial
moisture content, and the type and grade of poly-
urethane. Owing to the two-phase microstructure,
processing conditions significantly influence the mor-
phology and accordingly, the properties of the result-
ing component. The choice of optimum processing
conditions is also important for producing stress-free
products.
4. Recent Developments in Polyurethane Chemistry
Many conventional polyurethanes, particularly the
softer grades, are prone to unwanted degradation in
the biological environment. Use of polyurethanes in
pacemaker leads and breast implants has provided
much of the information on degradation. In Šitro tests
designed to mimic implant conditions, standard
chemical tests, and animal implants have provided
further evidence for propensity to degradation. Oxi-
dation and hydrolysis are the two major pathways of
degradation.
Polyester polyurethanes are not suitable for long-
term implant due to poor hydrolytic stability. This has
been largely overcome by the use of poly-
etherurethanes, with PTMO being the most common
polyether. However, soft grades of PTMO-based
polyurethane degrade when implanted for long
periods of time. Typically, degradation appears as
surface or deep cracking, stiffening, erosion, or de-
terioration of mechanical properties, such as flex–
fatigue resistance. This deterioration may ultimately
lead to implant failure.
The mechanism of biologically induced degradation
of polyurethanes has been the subject of much contro-
versy and research, which has been summarized in
reviews (Pinchuk 1994). Two mechanisms, enŠiron-
mental stress cracking (ESC) and metal-ion-induced
oxidation have been proposed. ESC requires both
stress and a chemical agent. Stress can be internal
stress from poor thermal processing or annealing or
it can be externally applied (e.g., from flexure in use
or compression around a suture). In PTMO-based
polyurethanes, the most susceptible site to oxidative
degradation is the –CH group adjacent to the either
#
oxygen. Within a given series, the softer polyurethanes
(containing more PTMO) are more prone to stress-
cracking than the harder grades (Szycher 1988). Metal-
ion-induced degradation is a significant problem
with implantable electrode leads, where metals of
high-oxidation potential such as cobalt and moly-
3
Polyurethanes in Biomedical Engineering
bdenum are in direct contact with polyurethane
insulation.
Many of the polyurethanes used in early medical
implants were not specifically designed for such
applications. However, the understanding from many
studies have provided valuable information for the
design of new polyurethanes for long-term implants.
Research efforts have mainly focused on the replace-
ment of PTMO by other macrodiols without func-
tional groups susceptible to oxidative and hydrolytic
degradation. The types of macrodiols investigated
include polycarbonate macrodiols (Pinchuk 1994,
Szycher et al. 1982), hydrocarbon macrodiols (see
review by Pinchuk 1994), polyether macrodiols with
fewer ether linkages than PTMO (Gunatillake et al.
1992), and siloxane-based macrodiols (Gunatillake
et al. 1999).
Hydrogenated poly(butadiene diol), poly(isobutyl-
ene diol), and macrodiols derived from predominantly
C-18 fatty acids or esters are the three main macrodiols
with a hydrocarbon backbone that have been investi-
gated for development of oxidation and hydrolysis
resistant polyurethanes. Polyurethanes from the first
two have not received serious consideration for medi-
cal implants, despite excellent hydrolytic and oxidative
stabilities. This may be a function of their poor
elastomeric behavior. The fatty acid based macrodiols
can be prepared by dimerization of C-18 fatty acids via
Diels–Alder or other coupling reactions, and reducing
the resulting mixture of diacids or esters to form a diol.
The diols can be reacted with aliphatic diisocyanates
such as 1,4-cyclohexane diisocyanate and diol chain
extenders. These polyurethanes have been claimed to
be biostable based on animal implant experiments. A
limitation of these polyurethanes was the difficulty in
achieving low flex modulus; the modulus of the softest
grade was similar to that of a hard grade of a PTMO-
based polyurethane.
m
n to achieve this include: (i) incorporation of PDMS as
5 a surface modifying end-group or covalent binding of
Polyurethanes based on MDI, butanediol, and
higher macrodiols (e.g., poly(hexamethylene oxide),
poly(octamethylene oxide), and poly(decamethylene
oxide) (n l 6, 8, and 10 in 5, respectively)), offered
significantly improved stability over their PTMO
counterparts. These macrodiols can be prepared by
the acid-catalyzed condensation polymerization of
the corresponding monomer diols. This polymeri-
zation technique can be easily adapted to
prepare macrodiols from diols that do not cyclize
easily under acidic conditions, and typically 1,6-
hexanediol and other diols of higher molecular weight
are suitable. The polyurethanes produced from these
higher macrodiols were more resistant to biologically
induced stress-cracking compared with PTMO-based
4
control and commercial materials, Pellethane 2363-
80A, Biomer, and Tecoflex EG80A, as shown by
implantation in sheep.
Increasing the macrodiol CH : O ratio caused an
# and a decrease in
increase in stiffness and hardness,
elongation and clarity. The differences, however, are
relatively minor in the case of poly(hexamethylene
oxide) and clear, flexible, degradation-resistant
materials of Shore 90-95A hardness are possible.
n
6
Polycarbonate macrodiols, based on hexamethylene
carbonate and copolymers thereof (6), have also been
claimed to impart good stability, although there
appears to be a limit of softness below which degra-
dation takes place. Carbothane, Corethane, and
Chronoflex are examples of trade names for poly-
urethanes based on these types of polycarbonate diols.
Accelerated tests carried out in rabbits for up to 6
months have shown that Corethane is significantly
more resistant to ESC than Pellethane 80A. Sub-
sequent studies on polycarbonate-based aliphatic
polyurethane (Chronoflex AL 80A) samples, however,
have reported up to 86% failures (appearance of
groves to shallow cracks) in experiments after 1 year of
implant. Although in this study Chronoflex AL 80A
performed better than Pellethane 80A, it creates some
doubt as to the long-term biostability of poly-
carbonate-based polyurethanes.
Incorporation of siloxane segments, poly(dimethyl-
siloxane), (PDMS) in the polyurethane matrix has
received considerable attention because of the proper-
ties of PDMS, which include high flexibility, good
hemocompatibility, excellent thermal and oxidative
stability, and low surface energy. The main approaches
silicones as a surface coating, and (ii) incorporation of
PDMS into the polyurethane backbone as part of the
soft segment as well as the hard segment.
Siloxane-rich surfaces can be achieved by modifying
the end groups of polyurethanes by covalent attach-
ment of monofunctional siloxanes (Ward 1995). Due
to their low surface energy, the siloxanes migrate to
the surface. However, under high strain the effective-
ness of such a surface layer to protect a degradation
prone bulk of the polyurethane has not been demon-
strated. Covalent binding of silicone rubber on to a
polycarbonate urethane has enhanced biostability
(Pinchuk 1994).
A significant advance in the design of degradation
resistance has been the development of methods to
incorporate high levels of siloxane as part of the linear
polyurethane structure. Early studies (Speckhard and

Cooper 1986) showed that the preparation of such
polyurethanes is not straightforward due to incom-
patibility between nonpolar siloxane segments and
polar hard segments, resulting in highly phase-
separated materials with poor mechanical properties.
Among several strategies reported to improve seg-
mental compatibility, the incorporation of a small
amount of a second macrodiol (comacrodiol) is
effective for preparing siloxane-rich polyurethanes
with good mechanical properties (Gunatillake et al.
1999). In this strategy, a comacrodiol with appropriate
solubilizing properties, such as poly(hexamethylene
oxide), is used with a siloxane macrodiol, such as α,ω-
bis(6-hydroxyethoxypropyl) polydimethylsiloxane
(7), to improve the compatibility of hard and soft
phases. Further improvement can be achieved by
using silicon-based chain extenders (e.g., 1,4-bis(4-
hydroxybutyl)tetramethyldisiloxane) (8). This results
in very flexible, low-modulus polyurethanes, com-
parable with some grades of silicon rubber, but with
significantly better tensile and tear strength.
n
7 microscopy (SEM). Determination of changes in
8 degradation.
The method of synthesis has a significant effect on
morphology and properties of siloxane-based poly-
urethanes. However, both one- and two-step poly-
merization methods can be successfully adapted to
prepare polyurethanes with good mechanical proper-
ties and processability. In the one-step process, the use
of a catalyst such as dibutyltindilaurate is essential to
prepare materials with good mechanical properties. In
contrast, the two-step process requires no catalysts,
and has the advantage of reduced leachables. Such
polyurethanes can be easily processed by conventional
techniques such as extrusion, injection molding, com-
pression molding, and solvent casting. The high
siloxane content allows thermal processing without
additives such as bisethylenestearamide waxes.
The biostability of the new siloxane-based poly-
urethanes (Elast–Eon) has been assessed by a number
of implant experiments (Gunatillake et al. 1999,
Rhodes et al. 1999) using dumbbell shaped specimens
in a stressed configuration (250% strain) for 3 months
in sheep. In these experiments Pellethane 2363-80A
and Pellethane 2363-55D were used as negative and
Polyurethanes in Biomedical Engineering
positive controls, respectively. Results of these experi-
ments have demonstrated that new siloxane-based
polyurethanes have superior biostability.
5. In vitro and in vivo Testing
The selection or formulation of polyurethanes for
specific medical applications requires extensive testing
of the material.
Many in Šitro test procedures for assessing bio-
stability are designed either to accelerate or simulate
likely hydrolytic and oxidative environments in ŠiŠo
(see review by Pinchuk 1994). These tests include
incubation of test specimens in enzymes of which the
most widely tested are papain, trypsin, and esterase.
The others include chemical agents to induce oxidative
and hydrolytic conditions, and the most commonly
used reagents are strong acids and bases, metal salts
such as cobalt chloride, silver chloride, and hydrogen
peroxide. The specimens are immersed in the test
solution, typically at 37 mC for various lengths of time,
ranging from a few days to a few weeks. Elevated
temperatures and tensile straining of test samples are
also commonly used to accelerate degradation. The
most widely used method to assess degradation is the
examination of test specimens under scanning electron
molecular weight and tensile properties are also used
to assess degradation, but when the degradation is
localized to some areas on the surface such measure-
ments are not very useful. Infrared spectroscopy is
used to assess structural changes resulting from
A comparatively simple accelerated in Šitro test
(Zhao et al. 1995) involves the exposure to peroxide–
cobalt chloride solution in contact with glass wool.
Under these conditions PTMO-based polyurethane
Pellethane 2363-80A produced deep cracking in only a
matter of weeks, where several months are required
in ŠiŠo to show similar cracking. These in Šitro
tests are mainly used for screening of experimental
polyurethanes.
Owing to the complexity of biological systems and
the complex cellular interactions at the tissue-bio-
material interface, which can vary from one material
to another, it is impossible to predict the durability of
polyurethanes based on in Šitro test results alone.
While, in Šitro results often predict failure, and relative
propensity to degradation via a given mechanism,
passing the test does not imply stability. The most
reliable test for biostability of new promising materials
is an accelerated test under appropriately controlled
implant conditions. Sheep, rats, and rabbits are
commonly used animal models. For acceleration of
degradation, the test specimens are frequently strained
over a suitable mandrel. In one method (Szycher 1988)
the polyurethane is fabricated into a thin-wall tubing
5
Polyurethanes in Biomedical Engineering
and strained over a mandrel up to strains of 400%, the
ends are tied, and then implanted. In another method
(Brandwood et al. 1994), dumbbells are punched from
a compression-molded sheet, stretched over Perspex
sample holders to 250% of their resting length and
then implanted. The duration of the implant periods
varies from a few weeks to 6 months. Explanted
samples, after cleaning to remove biological debris,
are examined by SEM for degradation. Severe degra-
dation is easily visible, in extreme cases disintegration
of the test specimen is observed. Typically most
literature reports provide SEM pictures of selected
areas with comments as evidence for degradation,
which sometimes is not sufficient to assess the relative
stabilities of different materials. Another method
(Meijs et al. 1997) provides a ranking system suitable
for comparison of the extent of degradation of
different materials. It is important to understand that
SEM is sensitive for the detection of ESC; cross-
checking for degradation by other mechanisms (e.g.,
hydrolysis) through IR or molecular weight changes is
important.
Unambiguous quantitation of surface and bulk
chemical changes in explanted polyurethanes is gen-
erally difficult due to limitations in analytical tech-
niques and the difficulty associated with interference
from biological residues that contaminate sample
surfaces. A technique based on cryomicrotomy and
FTIR microscopy (McCarthy et al. 1997) is useful
to study subtle chemical changes associated with
degradation of implanted materials. The technique
is useful to section and analyze localized areas
of degradation, providing valuable information to
understand underlying degradation mechanisms.
6. Concluding Remarks
The excellent physical properties, the relative ease of
fabrication into devices, and the wide range of proper-
ties that can be achieved, make polyurethanes the
elastomer of choice for many implant applications.
Recent advances in polyurethane design and synthesis
have identified key structural features responsible for
long-term biostability. These understandings should
help custom design polyurethanes for specific appli-
cations. However, there is always the cautionary note,
that it remains to be seen whether the new materials
will perform clinically as well as they are predicted to
on the basis of in Šitro and in ŠiŠo animal model testing.
The development of test protocols that predict long-
term biostability of polyurethanes still remains an area
for continued research, as is a full understanding of the
molecular mechanisms of degradation.
6
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 Polyurethanes in Biomedical Engineering

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