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14 Rubber & Plastics News ● November 1, 2010
BioIsoprene for use in renewable alternatives
By Frank J. Feher,
Goodyear
Marguerite Cervin,
Anthony Calabria, Gregg Whited
and Andrei Miasnikov
Genencor International Inc.
About 10 million metric tons (20 bil-
lion pounds) of natural rubber are pro-
duced annually,1 most of which is collect-
ed from trees in relatively undeveloped
countries within several hundred miles
of the equator.
About half of the global natural rub-
ber supply is used to make tires, which
on average contain approximately equal
amounts of natural rubber and petrole-
um-derived synthetic rubber.
As the economies in Asia have grown
rapidly, both demand for natural rubber
and its price have increased dramatically.
In fact, the supply and price issues as-
TECHNICAL NOTEBOOK
Edited by Harold Herzlichh
sociated with both natural rubber and
petroleum-derived synthetic rubber
have become eerily similar to those ob-
served for oil: supply is inherently limit-
ed, demand is growing rapidly, and
nearly all of the material must be im-
ported from a relatively small number of
countries with potentially unreliable
supplies.
Industries dependent on inexpensive
imported natural rubber also face three
additional threats with potentially cata-
strophic consequences.
The first is accidental or intentional
introduction of South American leaf
blight into the growing region responsi-
ble for more than 90 percent of the
world’s rubber supply.
This fungus was a major problem in
Brazil’s rubber-growing regions and
could rapidly devastate Asia’s rubber
trees,2 which are all derived from the
same species (Hevea brasiliensis).
The other two threats stem from the
fact that most rubber is collected by rel-
atively poor people in underdeveloped
countries.
If these countries undergo substantial
economic development, there might be
fewer incentives for people to collect
rubber and strong incentives to plant
much more productive crops, such as
food or palm oil for fuel.
If on the other hand these countries
remain underdeveloped and there is a
flu pandemic, it seems possible based
on earlier flu pandemics3 that rubber-
producing countries might suffer dis-
proportionately greater than devel-
oped countries and that the natural
rubber supply chain might be greatly
disrupted.
All of these issues seemed to converge
in 2006 as the global economies were
booming, oil prices were climbing to-
ward $150 a barrel, natural rubber
prices were more than $1 per pound,
geopolitical tensions were rising, and
Asia was struggling to prevent the
spread of a flu virus similar to the one
responsible for killing an estimated 50
million to 100 million people in 1918.
It was against this backdrop that
Goodyear launched its most ambitious
effort since WWII to develop dependable
sources of rubber from domestic U.S.
feedstocks.
As outlined below, this effort seeks to
leverage recent advances in industrial
biotechnology to produce large amounts
of synthetic polyisoprene from the
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Technical
More recently, advances in molecular
biochemistry and industrial biotechnolo-
Executive summary gy present two other tantalizing possi-
Rubber is a critical and strategic industrial raw material for manufacturing a bilities for developing useful materials
wide variety of products, ranging from medical devices and personal protective to replace Hevea rubber.
equipment to aircraft tires. The first involves production of natural
Presently, nearly all major manufacturers of rubber goods are dependent on rubber via genetically-modified plants or
either imported natural rubber from Hevea brasiliensis (i.e., the Brazilian rub- micro-organisms containing the key rub-
ber tree) or petroleum-based synthetic polymers as feedstocks. ber-producing enzymes found in Hevea
Unfortunately, neither material is obtainable from domestic U.S. sources in brasiliensis.
quantities sufficient to meet anticipated future demand. Although it has be argued that this
In 2008, Goodyear and Genencor, a division of Danisco A/S, announced a pro- approach would not be economically vi-
gram to co-develop BioIsoprene-brand material as a revolutionary bio-based al- able for microbial fermentation,8 extrap-
ternative to the petroleum-derived chemical compound isoprene. olation of Metabolix’s technology9 for
BioIsoprene can be used for the production of synthetic elastomers and rub- producing high-grade thermoplastic
ber, which in turn are alternatives to natural rubber. polyesters in plants clearly suggests
The development of BioIsoprene could make the tire and rubber industry less that it might be possible to produce com-
dependent on oil-derived products, such as synthetic rubber made from petrole- parable particles of cis-PI in genetically
um-derived isoprene or butadiene. engineered plants.
This paper provides an overview of current efforts to develop BioIsoprene, The second possibility is to produce
ranging from the early motivations for developing BioIsoprene to the most re- synthetic rubber from monomers (e.g.,
cent technical accomplishments. isoprene, butadiene, styrene) derived
from industrial fermentation of the same
feedstocks being considered for fermen-
same biorefinery feedstocks being de- of natural rubber used in tires, even tation-based production of biofuels.
veloped for large-scale production of though synthetic PI would be a suitable Although, in principle, it should be
biofuels, such as bioethanol, biobutanol replacement for natural rubber for possible to develop large-scale replace-
and biodiesel. many applications. ments for Hevea rubber based on all of
Approaches for replacing NR Table I. Two known biochemical pathways for producing isoprene.
During and since WWII, research
done to develop alternatives to Hevea
natural rubber identified three promis-
ing domestic U.S. sources for rubber:
1. Cultivation of rubber from guayule
latex (Parthenium argentatum)4
2. Cultivation of rubber from roots of
the Russian dandelion (Taraxacum kok-
saghyz)5
3. Production of synthetic polymers
from petroleum-derived monomers,6 es-
pecially isoprene, butadiene and
styrene.
The first two sources are noteworthy
because both were: (a) explored exten-
sively by the U.S. during the 1940s; (b)
shown to be useful for tire applications
when Hevea rubber is not available; (c)
abandoned in favor of Hevea rubber and
synthetic rubber after WWII; and (d) re-
cently reintroduced as modern replace-
ments for imported Hevea rubber.
The third approach—synthetic poly-
mers from petroleum-derived mono-
mers—ultimately prevailed as the most
attractive alternative to Hevea rubber
because its appeal was irresistible dur-
ing the golden age of petrochemical re-
search, when U.S. supplies of petroleum
were plentiful and energy was inexpen-
sive.
At the time, polymer chemists had lit-
tle appreciation for what they didn’t
know about the structure of natural rub-
ber7 and they had not yet realized that it
would be extremely difficult (impossi-
ble?) to make a true natural rubber re-
placement based solely on polymers or
copolymers of hydrocarbon monomers.
Nevertheless, early investments in
synthetic polymer research paid big div-
idends by providing commercially viable
routes to several large-volume synthetic
rubbers that are now widely used in the
tire industry, including styrene-butadi-
ene rubber and synthetic cis-polyiso-
prene (synthetic PI).
Of all of these synthetic rubbers, syn-
thetic PI (e.g., Natsyn) has properties
that are most similar to natural rubber
because its chemical composition and
structure are most similar to natural
rubber.7
Unfortunately, the isoprene monomer
required to make synthetic PI has al-
ways been scarce relative to the amount
RPN20101101P015.qxp 10/27/2010 3:10 PM
www.rubbernews.com
the approaches described above, each
of these approaches presents a num-
ber of unique technical and business
risks.
In the case of guayule, Russian dande-
lion and other crop-based approaches,
there are many obvious challenges asso-
ciated with developing an integrated
supply chain for growing, harvesting
and processing large volumes of plant-
based feedstocks into finished rubber.
These kinds of challenges require co-
ordinated action by a large number of
people and agencies, and they are noto-
riously difficult to overcome without tru-
ly compelling business cases or aggres-
sive government support.
The USDA is working with companies
(e.g., Yulex Corp.) to lay the foundation
for domestic production of rubber crops,
but it still is likely to take many years be-
fore large amounts of domestic rubber
would become available for tire produc-
tion.
There also are considerable technical
risks associated with developing Hevea
replacements based on rubber-produc-
ing crops or micro-organisms.
First and foremost, there are big dif-
ferences between natural rubbers de-
rived from different sources.7
Are any of these materials suitable as
a replacement for Hevea rubber in to-
day’s applications? And if the perform-
ance of these materials is not on par with
Hevea rubber, what options are avail-
able for closing any performance gaps?
Would it be easy to re-engineer a
plant or microorganism to provide more
desirable rubber properties, such as tear
strength or rate of strain crystalliza-
tion?
Could this be done quickly and cost-ef-
fectively without compromising the more
desirable characteristics of the plant or
micro-organism, especially the rubber
yield and the cost to produce rubber?
While it’s true that it never has been
easier to engineer crops or micro-organ-
isms, it is equally true that the demands
placed on the performance of natural
rubber are much higher than they were
in the 1940s and ’50s.
Cost-effectively producing rubber
from plants or micro-organisms is only
half the battle.
Any large-volume replacement for He-
vea rubber must have properties suffi-
ciently similar to Hevea rubber to allow
its use without compromising perform-
ance.
Fig. 1. Schematic outlining construction of an engineered micro-organism using re-
combinant DNA techniques. In this case, the isoprene synthase gene in a geneti-
cally modified yeast plasmid is replaced by a synthetic Kudzu isoprene synthase
gene.
Page 1
Technical
The BioIsoprene option
As Goodyear was evaluating options
for developing alternatives to imported
natural rubber, the U.S. announced its
intention to aggressively fund develop-
ment of technology for producing
ethanol from cellulosic materials.
In fact, the stated U.S. goal was to
make cellulosic ethanol “practical and
competitive within six years,” or by
2012.10
This announcement, which occurred
during President Bush’s 2006 State of
the Union address, seemed reminiscent
of President Kennedy’s earlier challenge
to put a man on the moon by the end of
the 1960s.11
The challenge was Herculean, and the
government clearly was willing to spend
the resources necessary to attract and
mobilize the talent required to deliver
such an ambitious goal.
As we contemplated the significance
and likely impact of the U.S. effort to ac-
celerate commercialization of cellulosic
ethanol technology, we realized that the
feedstocks being considered for biofuel
production might be attractive for pro-
ducing monomers for synthetic rubber.
In particular, we wondered whether it
might be possible to produce “cellulosic
isoprene” via industrial fermentation of
sugars derived from cellulose.
If this was true and bioethanol indeed
could be made inexpensively via indus-
trial fermentation, it seemed reasonable
that production of “bioisoprene” also
might be commercially viable on a scale
large enough to make enough synthetic
polyisoprene to replace substantial
quantities of natural rubber in tires.
Our concept for replacing Hevea rub-
ber with synthetic PI derived from
BioIsoprene quickly gained momentum
as we examined the known literature.
We already were aware that isoprene
is a naturally occurring hydrocarbon
produced by a broad range of plants and
animals,12 so we knew that biochemical
pathways existed for producing it.
We soon learned that there are, in
fact, two known pathways for producing
isoprene: the MVA (i.e., mevalonic acid)
pathway13 and the DXP (i.e., deoxy-xylu-
lose phosphate) pathway.14 (See Table
I) .
Glucose can be metabolized to inter-
mediates in both pathways,15 and both
pathways produce isoprene from the
same intermediate (DMAPP).
It also was known from labeling ex-
Rubber & Plastics News ● November 1, 2010 15
periments with 13C-glucose that all car- Similarly, numerous methods were
bon atoms in isoprene are derived from evaluated for recovering BioIsoprene
glucose.16 from fermentation off-gases, and de-
Collectively, all of these results sup- tailed analyses of impurity profiles were
ported our concept for developing a performed to develop methods for pro-
large-scale replacement for Hevea rub- ducing isoprene samples suitable for
ber based on synthetic polyisoprene de- polymerization.
rived from BioIsoprene. In short order, the strain develop-
In light of Goodyear’s extensive histo- ment teams were producing BioIso-
ry as a major producer of both petrole- prene at levels well-above those previ-
um-based isoprene and synthetic poly- ously reported in the literature,17 the
isoprene, a BioIsoprene-based approach recovery team was regularly isolating
for replacing natural rubber is very at- synthetically useful quantities of
tractive. BioIsoprene, and the purification and
Most importantly, Goodyear has ex- polymerization team was demonstrat-
tensive experience with both isoprene ing that it could make polyisoprene
and synthetic polyisoprene. analogous to commercially available
In addition to knowing how to produce synthetic rubber.
polymer-grade isoprene and numerous Since that time and in spite of chal-
synthetic polyisoprene rubbers, it knows lenging economic circumstances, Goody-
well the extent to which Hevea rubber ear and Genencor have made steady
can be replaced by synthetic polyiso- progress toward developing an integrat-
prene in a broad range of tire applica- ed process to manufacture BioIsoprene.
tions. Large-scale industrialization could be
Goodyear does not have the technical ready as soon as 2013, with Genencor
expertise to develop a process for pro- leading commercial development.
ducing isoprene via industrial fermen-
tation; however, it has an excellent un- A closer look
derstanding of the business and Development of an integrated
technical risks associated with develop- process for producing, recovering and
ing a large-scale replacement for natu- purifying BioIsoprene presents many
ral rubber based on synthetic polyiso- challenges, but none is greater than
prene. that posed by engineering micro-organ-
BioIsoprene clearly represented a isms to produce commodity hydrocar-
great opportunity to develop a domes- See BioIsoprene, page 16
tic, non-petroleum-based alternative to
imported rubber, if Goodyear could
find the right technology partner to de-
velop the industrial fermentation
process.
Development
After evaluating a number of poten-
tial technology partners, Goodyear
agreed to join forces with Genencor, a
Danisco division, to pursue joint devel-
opment of BioIsoprene.
Genencor was particularly attractive
because of its U.S. leadership in indus-
trial biotechnology, track record for com-
mercial successes, and focus on total
process development.
It also had strong R&D programs with
broad core competencies in industrial
biotechnology.
With Genencor leading efforts to pro-
duce BioIsoprene via fermentation and
Goodyear leading efforts to recover and
purify BioIsoprene, the collaboration
quickly gained momentum.
For example, multiple strains of iso-
prene-producing micro-organisms were
produced by incorporating genes from
isoprene-producing plants into micro-or-
ganisms that were genetically engi-
neered to produce large amounts of the
metabolic intermediates required for
isoprene biosynthesis.
The author
Frank J. Feher is a senior re-
search and development associate
at Goodyear’s Global Tire Materi-
als unit, where he conceived the
idea for developing a large-volume
replacement for natural rubber
based on BioIsoprene.
He began working at Goodyear
in late 2002 as a senior scientist
and internal consultant for devel-
opment of new technology within
Goodyear’s former Chemical Divi-
sion. Before Goodyear, Feher
spent 17 years as a chemistry pro-
fessor at the University of Califor-
nia, Irvine.
He can be reached at frank_fe-
her@goodyear.com.
RPN20101101P016.qxp 10/27/2010 3:28 PM
16 Rubber & Plastics News ● November 1, 2010
BioIsoprene
Continued from page 15
bons with a cost structure competitive
with existing petroleum-based hydro-
carbons.
This can only be accomplished by ag-
gressively engineering robust micro-or-
ganisms to maximize flow of carbon
through the isoprene-producing path-
ways.
Specific details about how this can be
accomplished are provided in reference
18 and the references cited therein.
In general terms, the process for engi-
neering isoprene-producing micro-or-
ganisms can be understood by referring
to Table I and Fig. 1.
Table I illustrates the two known bio-
chemical pathways for producing iso-
prene. Either can function in isoprene-
producing cells and microorganisms.
For micro-organisms naturally using
the MVA pathway for isoprenoid biosyn-
thesis, the steps leading from Acetyl-CoA
to isoprene are identical, but the enzymes
responsible for catalyzing these reactions
often have slightly different structures.
These differences do not change the
overall mechanism for producing iso-
prene, but they often influence the rela-
tive rates of the individual reactions in
the mechanism.
This allows other reactions to compete
more favorably for the intermediates
generated by the MVA pathway, which
in turn provides a means for different
organisms to use similar biochemical re-
actions to produce very different mix-
tures of biological molecules.
All of the information required for an
organism to make its enzymes needed
for catalyzing the MVA pathway is en-
coded in its genes.
If an organism makes little or no iso-
prene via the MVA pathway, this is ei-
ther because the organism’s genes lack
codes for one or more of the enzymes re-
quired to produce isoprene, or because
the enzymes created from these codes
are poor catalysts for one or more reac-
tions leading to isoprene.
The key to engineering a useful micro-
organism for production of BioIsoprene
is to incorporate genes from more effi-
cient isoprene-producing organisms into
a robust host that is capable of main-
taining its own survival while generat-
ing large amounts of isoprene. If neces-
sary, it is even possible to incorporate
synthetic genes to influence the rate of
expression of an enzyme or modify genes
to influence the rate or specificity of the
reactions.
An example of genetically engineering
micro-organisms can be gleaned from
Fig. 1. In this figure the diagram repre-
sents a plasmid which contains genetic
information that allows it to replicate in
micro-organisms.
The diagram in the upper right repre-
sents a synthetic kudzu ispS gene se-
quence. The ispS gene encodes the Iso-
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Page 1
Technical
prene synthase, the enzyme required to
produce isoprene from DMAPP. This
ispS gene is cloned into the plasmid and
introduced into micro-organisms.
Because all micro-organisms produce
DMAPP, the introduction of the ispS
gene now allows them to produce iso-
prene.
Similar strategies can be used to mix
and match genetic material from a
broad range of micro-organisms that can
either produce isoprene or support pro-
duction of isoprene.
Prior to Genencor’s work, previous ef-
forts to produce isoprene via fermenta-
tion produced only very small amounts
of isoprene.17
As a result of Genencor’s work, this
situation has changed dramatically.
This is best illustrated by Fig. 2,
which corresponds to the data in Figs.
78A, 78B and 78D in reference 18.
This figure contains data from a glu-
cose-fed fermentation performed at 34°C
in a 15-L bioreactor with genetically
modified E. coli cells containing genes
from other organisms, including the iso-
prene synthase gene from P. alba (i.e.,
the white poplar tree).
Fig. 2 shows the cell density profile
within the bioreactor, which exponen-
tially increases during the growth phase
and is followed by a stationary phase.
The isoprene titer increased over the
course of the fermentation to a maxi-
mum value of 33.2 g/L at 40 h (and 48.6
g/L at 59 h). Finally, the total amount of
isoprene produced by the fermentation
is shown, which was 281 g after 40
hours and 451 g after 59 hours (Fig. 2).
These now dated results convincingly
show that it indeed is possible to engi-
neer microorganisms for production of
BioIsoprene.
Since these experiments were first de-
scribed, the state-of-the-art has contin-
ued to advance. Goodyear and Genencor
now are on track to have an integrated
process ready to manufacture BioIso-
prene on an industrial scale as early as
2013.
Conclusion
The development of BioIsoprene repre-
sents a major achievement for industrial
biotechnology because it has the poten-
tial to provide enormous quantities of a
basic hydrocarbon that, in principle, can
be used as a feedstock for a large number
of value-added products. One of these
products is synthetic cis-polyisoprene,
which for decades has been recognized as
a suitable replacement for natural rub-
ber in many applications.
The BioIsoprene process being pio-
neered by Goodyear and Genencor final-
ly offers the very real possibility for ob-
taining the quantities of low-cost
isoprene needed to produce a meaning-
ful large-volume alternative to Hevea
natural rubber.
Acknowledgements
This project would not have been pos-
sible without support and collaboration
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Fig. 2. Time course data of E. coli cells expressing heterologous MVA pathway and
isoprene synthase genes and grown in a 15-L, glucose fed-batch bioreactor at
34°C. The black diamonds show the isoprene titer profile over the course of the cell
culture. The black squares show the total isoprene produced during the fermenta-
tion. The open circles show the cell density profile within the bioreactor as meas-
ured by optical density at a 550 nm wavelength.
from a large number of talented people ka, Y.; Sakdapipanich, J. T. Structure and Origin of
Long-Chain Branching and Gel in Natural Rubber.
from Goodyear and Genencor. KGK, Kautschuk Gummi Kunststoffe 2005, 58, 115-
We are especially grateful for the con- 22. (in English)
tributions made by the early project team. 8. Mooibroek, H.; Cornish, K. Alternate Sources of
For Goodyear, this team included Aaron Natural Rubber. Appl. Microbiol. Biotechnol. 2000,
53, 355-65.
Puhala, Len Sikora, Erin Webster, Meg 9. Bohmert, K.; Peoples, O. P.; Snell, K. D. Metabol-
Noethen, Tim Sabo, Tang Wong, Stephan ic Engineering: Plastids as Bioreactors. In Molecu-
Rodewald, Dave Zanzig, David Benko, lar Biology and Biotechnology of Plant Organelles;
Jesse Roeck and Bill Hopkins, who enthu- Daniell, H., Chase, C. D., Eds.; Kluwer Academic
Publishing: Netherlands, 2004, p 559-585.
siastically served as Goodyear’s execu- 10. President G. W. Bush, State of the Union Ad-
tive-level champion during the project’s dress, January 31, 2006 (http://www.npr.org/tem-
critical embryonic stage. For Genencor, plates/story/story.php?storyId=5181905)
this team included Karl Sanford and Rich 11. President J. F. Kennedy, Speech to Congress, May
25, 1961 (http://history1900s.about.com/od/1960s/a/jfk-
LaDuca. moon.htm)
12. Sharkey, T. D.; Yeh, S. Isoprene Emission from
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