NatureWorks Ingeo Polylactide: Past, Present and · PDF file · 2016-08-18for...
Transcript of NatureWorks Ingeo Polylactide: Past, Present and · PDF file · 2016-08-18for...
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NatureWorks Ingeo™ Polylactide:
Past, Present and Future
RC Bopp
NatureWorks LLC
Minnetonka, MN
IOWA STATE UNIVERSITY
BIOPOLYMERS & BIOCOMPOSITES WORKSHOP
August 14, 2012
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• NatureWorks: Who we are and what we do
• Early History
• Bioplastics Value Proposition
• Ingeo EOL Value Proposition
• Further Look into the Future
Agenda
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Who We Are . . .
• 1st world-scale
biopolymer producer
• Economies of scale to
compete in traditional
plastics markets
(140,000 MT capacity)
• Peer reviewed eco-profile (LCA)
• Global plastics & fibers customer
base
• Ingeo applications breadth across
many markets, geographies, and
retail applications
• Privately owned by Cargill Inc and
PTT Global Chemical
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Our Customers
sugar (dextrose)
Plants
Carbon dioxide
and water
manufacturing
Where it comes from….natural plastic from plants, not oil
What We Do . . .
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5
O
OH
OH
HO
CH2HO
OH
HO
OH
O
CH3H
O
OH
OH
O
CH2HO
O
n
Starch Dextrose
(Glucose)
Lactic Acid
Hydrolysis
O
O
O
CH3H
n
2
PLA
Chemical Processing
Polylactide Synthesis
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6
D-Lactic Unit L-Lactic Unit
220o C
180o C
Creating a Family of Polymers
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Early History of Polylactide Polymers
– Lactide monomer production described in 1912
– Polylactide production described in 1932 (W.H. Carothers et al.)
• Technology developed further by DuPont, with high molecular weight polymers in
1955, but technology appears to have been shelved
• First commercial application c.1972, with Ethicon Inc. development of resorbable
sutures (poly-lactide-co-glycolide)
– Resurgence of interest in 1980’s
• E.S. Lipinsky, “Chemicals from Biomass: Petrochemical Substitution Options”,
Science, 212, 1465-1471 (1981) (Battelle Columbus Laboratories)
• E.S. Lipinsky and R.G. Sinclair, “Is Lactic Acid a Commodity Chemical?”, Chem. Eng.
Progress (Aug. 1986)
– Cargill project started in 1989
– Commercial production in Blair, Nebraska Dec. 2001
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By 1996 the field was heating up…. Company PLA capacity
(MM lb/yr)
Patent
activity
PLA approach Purity/ mol wt
control
Cargill (U.S.) 10 (100 MM lb/yr in
preliminary design phase,
not announced)
10 Ring opening
polymerization
Lactide distillation
Chronopol (US) 2 planned (1996) 56 Ring opening
polymerization
Crystallization/
melt crystallization
Shimadzu
(Japan)
0.2 22 Ring opening
polymerization
Lactide
crystallization,
solid state
polymerization
Mitsui Toatsu
(Japan)
2-20 planned 97 Direct
condensation
Solvent with water
removal
Neste OY
(Finland)
Not available 1 Direct
condensation
Reactive coupling
Adapted from D. R. Witzke Ph. D. thesis, 1997, Michigan State University
Capacity based on published news reports. Patent activity is worldwide published applications. Chronopol patents
assumed to include Battelle, EcoChem, Ecopol, and DuPont.
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It has been a complex journey…..
Project begins
at Cargill
Pilot plant
(5 lb/hr)
Semi-works plant
(1,000 lb/hr)
JDA Dow
Chemical
Cargill Dow
Polymers, LLC (JV)
NatureWorks LLC
(Stand Alone JV)
Cargill acquires Dow’s
interest in NatureWorks
Blair, NE
(20,000 lb/hr)
Polysar
JDA
NatureWorks jointly owned
by Cargill and Teijin
Wholly owned
by Cargill
Blair, NE
(40,000lb/hr)
’89 ’90 ‘91 ’92 ’93 ’94 ’95 ’96 ’97 ’98 ’99 ’00 ’01 ’02 ’03 ’04 ’05 ’06 ’07 ’08 ‘09 ’10 ‘11 ‘12
.AmberWorks
JV w/ BioAmber
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A Cycle of Innovation
Innovation:
People implementing new
ideas to create value.
Requires:
People using new knowledge
and understanding to
experiment with new
possibilities in order to
implement new concepts that
create new value.
Adapted from Joyce Wycoff, Innovation Network,
Thinksmart.com
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
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0
100
N(P
rocess)
1984
1985
1986
1987
1988
1989
1990
1991
1992
1993
1994
1995
1996
1997
1998
1999
2000
2001
2002
2003
2004
2005
2006
2007
Priority year
Chart
Cycle 1.
’89 ’90 ‘91 ’92 ’93 ’94 ’95 ’96 ’97 ’98 ’99 ’00 ’01 ’02 ’03 ’04 ’05 ’06 ’07 ’08 ‘09 ’10
Cycle 1. (1989-1995)
Development of basic monomer
properties, polymer properties,
technology to purify lactide and to
control polymer molecular weight,
melt point, and stability.
Process technology developed.
Culminates in products available
for market development.
Development of processes
has initial peak in 1993-
1996, NatureWorks is
actively filing at same time.
Project begins in
Cargill
Pilot plant
(5 lb/hr)
Semiworks plant
(1,000 lb/hr) JDA Dow
Chemical
Blair, NE
(20,000 lb/hr)
Blair, NE
(40,000 lb/hr)
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0
100
200
300
400
500
N(E
nd-U
se)
1984
1985
1986
1987
1988
1989
1990
1991
1992
1993
1994
1995
1996
1997
1998
1999
2000
2001
2002
2003
2004
2005
2006
2007
Priority year
Chart
Cycle 2.
Cycle 2. (1996-2002)
Market development quantities of
IngeoTM are available. Polymer is
processed on commercial scale
lines. Process control and
manufacturing strategy are
refined. Culminates in design and
construction of full scale
manufacturing plant at Blair,
Nebraska.
Development of end
use applications
expands explosively,
peaking in 2000-2002.
Project begins in
Cargill
Pilot plant
(5 lb/hr)
Semiworks plant
(1,000 lb/hr) JDA Dow
Chemical
Blair, NE
(20,000 lb/hr)
Blair, NE
(40,000 lb/hr)
’89 ’90 ‘91 ’92 ’93 ’94 ’95 ’96 ’97 ’98 ’99 ’00 ’01 ’02 ’03 ’04 ’05 ’06 ’07 ’08 ‘09 ’10
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0
100
200
300
400
500
600
700
800
N(P
roduct)
1984
1985
1986
1987
1988
1989
1990
1991
1992
1993
1994
1995
1996
1997
1998
1999
2000
2001
2002
2003
2004
2005
2006
2007
Priority year
Chart
Cycle 3.
Cycle 3. (2003-2010)
IngeoTM available in standard
grades. End products are
developed and moved into retail.
New compositions, copolymers,
flow additives, color packages,
nucleants, inhibitors, etc. being
developed worldwide. New
investments in processing
equipment opens bigger markets*
and achieves economy of scale.
Development of new
products such as
copolymers,
compositions,
modifiers of all types
continues to expand.
*Historically, new polymers have averaged 11 yrs to reach
300 MMlb/yr sales from when commercial plant was
operational. C. Musso, Ph.D. (McKinsey)
Project begins in
Cargill
Pilot plant
(5 lb/hr)
Semiworks plant
(1,000 lb/hr) JDA Dow
Chemical
Blair, NE
(20,000 lb/hr)
Blair, NE
(40,000 lb/hr)
’89 ’90 ‘91 ’92 ’93 ’94 ’95 ’96 ’97 ’98 ’99 ’00 ’01 ’02 ’03 ’04 ’05 ’06 ’07 ’08 ‘09 ’10
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Cycle 4. A Quick Look at What’s New & What’s Next
‘08 ‘09 ‘10 ‘11 ’12 ’13 ’14 ’15 ’16 ’17 ’18 ’19 ’20 ’21 ’22 ’23 ’24 ‘25 ‘26 ’27
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
New knowledge
Implement
concepts
Produce new
value/ products
Develop
New concepts
Experiment/
New possibilities
New understanding
Our collective journey to a sustainable future.
New players enter PLA field
Production becomes global
Full complement of biobased
additives/ modifiers
Stereocomplex available in
market development quantities
Pilot development of 2nd
generation biopolymers and
biobased chemicals
Recycle infrastructure developed
and organics collection/
composting becomes widespread
Children today are in college and
in the workforce, innovating even
better ways to a sustainable
future.
Cellulosic feedstock in use at
commercial scale
Biorefinery campus, with multiple
ventures. On-site cogeneration,
minimal waste.
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Environmental (consumer, retail, brand owners)
• Lower carbon footprint, less energy usage
• Better end-of-life options (litter, landfill, incineration)
• Target: lower environmental footprint of plastics
• Oil vs. plants feedstock cost (stability)
• Carbon or waste taxation
• Target: create viable alternate product portfolio (plastics)
Economic (plastics value chain)
Value Drivers
for the Industry
Even in these
extraordinarily difficult
economic times, the
STRATEGIC
and
ENVIRONMENTAL
value drivers remain
strong
“A SIGN OF THE TIMES”
• Renewable feedstock vs. oil
• Reduce dependence on foreign oil
• Target: cellulosic bio-refinery concept (gas + plastics)
Strategic (governments)
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Review process
for new Eco-Profile
1. Publication in the Industrial Biotechnology
Journal, August 2010.
- Manuscript reviewed by several reviewers
- Update of our 2007 publication
2. Peer review by Dr. Ian Boustead of Boustead Consulting.
- Final report now available
3. Review by Dr. Alberta Carpenter of NREL followed by uploading the eco-profile as well as a process description into the US LCI database
Download:
- Spreadsheets with the data files
- Report giving description of Ingeo production process
Ingeo™ Technology Credentials
www.nrel.gov/lci
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138
120
113
80
77
73
59
50
42
35
87
82
0 20 40 60 80 100 120 140 160
Nylon 66
Nylon 6
Polycarbonate
PS (HIPS/GPPS Avg)
PET (SSP)
PET (amorphous)
LD Polyethylene
Polypropylene
PVC (suspension)
Ingeo 2005
Ingeo 2009 CIT (current tech)
Ingeo Target
From cradle to polymer factory gate
[MJ / kg polymer]
-50% Greenhouse Gases Greenhouse Gases Non-renewable energy use
7.9
9.1
7.6
3.2
2.1
1.9
1.9
2.0
1.3
0.8
3.4
3.4
0 1 2 3 4 5 6 7 8 9 10
Nylon 66
Nylon 6
Polycarbonate
Polystyrene (HIPS/GPPS Avg)
PET (SSP)
PET (amorphous)
LD Polyethylene
Polypropylene
PVC (suspension)
Ingeo 2005
Ingeo 2009 CIT
Ingeo Target
From cradle to polymer factory gate
[kg CO2 eq. / kg polymer]
-60%
Continuous improvement process
Ingeo 2005 Ingeo Current Ingeo Target
-50%
7.9
9.1
7.6
3.2
2.1
1.9
1.9
2.0
1.3
0.8
3.4
3.4
0 1 2 3 4 5 6 7 8 9 10
Nylon 66
Nylon 6
Polycarbonate
Polystyrene (HIPS/GPPS Avg)
PET (SSP)
PET (amorphous)
LD Polyethylene
Polypropylene
PVC (suspension)
Ingeo 2005
Ingeo 2009 CIT
Ingeo Target
From cradle to polymer factory gate
[kg CO2 eq. / kg polymer]
-60%
Greenhouse Gases Non-renewable energy use
Value drivers:
Economic Strategic
Environmental
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April 26, 2012 - OBAMA
ADMINISTRATION
UNVEILS “BIOECONOMY
BLUEPRINT” ANNOUNCES
NEW R&D INVESTMENTS
“The world is shifting to an innovation economy
and nobody does innovation better than America.”
—President Obama, December 6, 2011
“Decades of life-sciences
research and the development
of increasingly powerful tools
for obtaining and using
biological data have brought us
closer to the threshold of a
previously unimaginable future:
“ready to burn” liquid fuels
produced directly from CO2, …
plastics made not from oil but
from renewable biomass . . .”
Strategic (governments)
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Strategic (governments)
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2012 & Beyond: NatureWorks Looking Forward
Broadening Products
& Applications
Globalizing the
Manufacturing Platform
Monetizing the EOL
Value Proposition
Cellulosic
Feedstocks
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Blair, NE
Rayong Province, Thailand
2015 target: Ingeo bioresin structurally less expensive than PS (and PET)
In 2015 NatureWorks will have 2 Ingeo plants operational
– Supported by 3 feedstock sources (corn, sugar cane, cassava)
– Stronger global commercial organization
Rayong Province, Thailand
Blair, NE
Rayong Province, Thailand
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NatureWorks
Ingeo
Polylactides
Ingeo
Lactides
8000 Series - foam
7000 Series – ISBM Bottles
6000 Series – fibers/nonwovens
4000 Series - films
3000 Series – Injection Molding
2000 Series - Thermoforming
A comprehensive platform of
polymer grades with world
scale economies
Now offering polymer grade
Ingeo lactides to support further
global growth of the industry
To . . .
Broadening from
Ingeo
Polylactide
Lactic
Acid Lactide
Cost effective Ingeo production is via
the Ingeo lactide intermediate
Broadening Products
& Applications
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Food Serviceware
Nonwovens / Fibers
Rigids Films
Durables
Where we are in the Market
Lactides Bus. Dev.
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High-Heat Ingeo™ Hot Cup Lids High-Heat Ingeo™ Cutlery
International
Paper StalkMarket US Biopolymers StalkMarket
Ingeo™ High-Heat Technologies -
Food Service-Ware
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Biaxially Oriented Films Growth
• Taghleef Industries
successfully starts
production of NATIVIA™
• NATIVIA™ is based on
Ingeo™, and is 100%
made from renewable
resources
• NATIVIA™ is a
compostable film that
complies with EN13432
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iTunes Sony Bank, Inc. REI DaiNippon,
Mitsubishi Plastics
and Sony
Ingeo™ Based Card Technology
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Bormioli Vedat
Injection Stretch Blow Molded Technology
Extrusion Blow Molded Technology
Shiseido Shampoo Bottle Polenghi Lemon Juice Bottle
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Ahlstrom Huggies Elements
Naturals
Fibers / Nonwovens
GroVia
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Max Jenny Dave Andersen Hernandez Cornet
Apparel
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Ingeo in Japan
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LG Hausys zea® Wall Paper
0.2(T) x 1,060(W) × 15M(L)
Structure
Application
Roll type
-. Residential
-. Commercial
Backing
Paper
Ingeo
Ingeo in Korea
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Dent, scratch
resistant
No color change
by environmental
Eco-friendly
9.0(T) x75(W) × 900(L)
Water Resistant
Plywood
Ingeo Laminate
Structure
Application
Yellow Soil
Adhesive
-. Residential
LG Hausys, zea® Flooring, “Prestige” line
Ingeo in Korea
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• NatureWorks: Who we are and what we do
• Early History
• Bioplastics Value Proposition
• Ingeo EOL Value Proposition
• Further Look into the Future
Agenda
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End of Life Options
Incumbent
Plastics Ingeo™
Landfill
X X
Recycle
X X
Incineration
X X
Compost
X
Anaerobic
Digestion X
Feedstock
Recovery X
Food
Scraps
12.7%
Paper
31.0%
Glass
4.9%
Metals
8.4%
Plastics
12.0%
Wood
6.6%
Yard
trimmings
13.2%
Other
3.5%
Rubber,
leather &
textiles
7.6%
Total US MSW Generation (by material), 2008
250 Million tons (before recycling)
Source: Municipal Solid Waste in the US: 2008 Facts & Figures
Progressing New
After-Use Options 31.8 MM tons/year
Methane (x23 CO2) release in landfill
Food waste diversion:
From landfill to composting facility
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Paper
31.0%
Glass
4.9%
Metals
8.4%
Plastics
12.0%
Wood
6.6%
Yard
trimmings
13.2%
Other
3.5%
Rubber,
leather &
textiles
7.6%
Food
Scraps
12.7%
Total US MSW Generation
(by material), 2008
250 Million tons (before recycling)
Source: Municipal Solid Waste in the US:
2008 Facts & Figures
Plants
A Credible Closed Loop Solution
Exists Today In Seattle…
RENEWABLE ► SUSTAINABLE ► END-OF-LIFE ► COMPOST
End-of-Life Options
And Opportunities
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End of Life Options
Incumbent
Plastics Ingeo™
Landfill
X X
Recycle
X X
Incineration
X X
Compost
X
Anaerobic
Digestion X
Feedstock
Recovery X
Food
Scraps
12.7%
Paper
31.0%
Glass
4.9%
Metals
8.4%
Plastics
12.0%
Wood
6.6%
Yard
trimmings
13.2%
Other
3.5%
Rubber,
leather &
textiles
7.6%
Total US MSW Generation (by material), 2008
250 Million tons (before recycling)
Source: Municipal Solid Waste in the US: 2008 Facts & Figures
Progressing New
After-Use Options
30 MM tons/year
< 10% recycled (some PET bottles only)
Closed loop recycling vs. today’s
bottle ► package ► landfill
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Ingeo is a bio-polymer made from lactic acid
Ingeo
Polylactide
O O
O
O
O O
O
O H
H
Lactic Acid
Polymerization
Hydrolysis
A new paradigm for Cradle-to-Cradle materials recycle . . .
“Feedstock Recovery”
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• COP 15 main conference area:
Ingeo™ used in main hall carpeting
and Food Serviceware
• New Company, BIOCOR LLC, launched with a business
model founded on trading post consumer PLA in any format . .
.
Monetizing the EOL
Value Proposition
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• Who we are and what we do
• Early History
• Bioplastics Value Proposition
• Ingeo in the Market Today
• Ingeo 3801X
• Ingeo EOL Value Proposition
• Further Look into the Future
Agenda
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Latest Ingeo Business & Product Developments
• Extending the Ingeo Product / Applications Range
1. Ingeo Lactides
2. New High % L (> 0.3%D) Performance Grades
3. NatureWorks - BioAmber
Joint Venture
4. Arkema’s Rnew –
Partnering to produce
bio-based (& improved) Plexiglas
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Ingeo Platform Extension
Ingeo Platform: “Performance materials from renewable resources”
L-100 Lactide
L-300 Lactide
L-800 Lactide
M-3000 Lactide
Lactide
monomer platform
Family of
Monomers
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Ingeo Platform Extension
3 series Injection Molding
7 series ISBM – bottles, BM
6 series Fibers, Nonwovens
4 series Films, cPLA
2 series Thermoforming
8 series Foam
1st Gen (Lactic)
polymer platform
Ingeo Platform: “Performance materials from renewable resources”
Family of
Polymers
L-100 Lactide
L-300 Lactide
L-800 Lactide
M-3000 Lactide
Lactide
monomer platform
Family of
Monomers
3100 HP
3260 HP
6100 D
6260 D
Family of
High % L Polymers
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High % L Performance Polymers
Improved Nonwovens
• Reduced shrinkage and improved dimensional
stability
• Increased hydrolysis resistance
• Capable of higher heat set temperatures
• Higher Tm creates advantages in bi-
component systems
• Larger processing windows
Improved Durables
• Faster cycle times & higher production rates
for lower molded part cost
• 3-4x increase in bulk crystallization rate
• 15°C improvement in heat deformation
temperature vs traditional Ingeo grades
• ~30% higher modulus above Tg
• Increased hydrolysis resistance
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“Elongation”
“S
tiff
ne
ss”
Bio-based
Conventional Plastics
PET
PP
PS Starch
Lactic Acid based polymers
PE
Succinic Acid based polymers
Performance Properties
New compounded Ingeo grades
combining properties of succinic
and lactic acid polymer platforms
Broadening the Addressable
Ingeo Property Window
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Slide 46 ITR, February 2012
• Global commercial presence
• Established Ingeo customer
relationships
• Applications development
experience
• Breadth of markets
• Experience in commercializing
new-to-the-world polymers
• Novel resin compounding
intellectual property
• Award-winning biotechnology
• Renewable chemicals
delivering high performance,
low carbon footprint, cost
competitive, building blocks
The Joint Venture combines the best of both companies into an
entity tasked with developing a new family of bio-based
compounded Ingeo polymers
Basis of the JV
Partnership & Synergy
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New Developmental Grades Resulting from the JV
• Thermoforming
Grade
– Ingeo AW 240D
• Injection Molding
Grade
– Ingeo AW 300D
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Arkema’s Ingeo-based Plexiglas® Rnew resins
• Compounded alloys of Arkema / Altuglas
International’s PMMA and NatureWorks’ Ingeo
(durable product focus) Provide step change in impact performance (≈ PETG, PC)
Significant increase in chemical resistance ( > PC)
Drastic increase in processability
Reduced carbon footprint & cost
- All whilst incorporating bio-sourced
materials … without compromising
optics, scratch resistance, color
acceptance or surface aesthetics
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0
20
40
60
High impact
PMMA
Impact
PMMA
10%PLA
Impact
PMMA
20%PLA
Impact
PMMA
40%PLA
Impact
PMMA
60%PLA
PETG PC
Imp
act str
en
gth
(J)-
Multi-axial impact
• Formulation design allows for tailored solutions
• Extraordinary improvements in impact strength while maintaining
modulus and strength
• Impact performance comparable to PETG and PC
Acrylic
Acrylic / Ingeo Alloys PETG
PC
Synergistic Impact Modification Effect
Source: Altuglas International a subsidiary of Arkema International
Arkema’s Ingeo based Plexiglas® Rnew resins
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Cellulosic
Feedstocks
Where we are
Where we’re going
– Our footprint is small: At full capacity, Ingeo™ represents:
• < 0.2 % of 2007 US corn production (< 0.05 % of global corn production)
– Ingeo technology is feedstock Agnostic. 2nd plant will use most
abundant local industrial sugar or starch source
– 2nd Generation is becoming an industrial reality
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Abengoa - Spain Myriant - Louisiana
Verenium - Louisiana • US government strongly supports
cellulosic bio-refinery concept
• Various feedstocks being evaluated
• Questions:
• Timing of first bio-refineries?
• Economics of bio-refineries?
Switching from 1st to 2nd generation feedstock will be as
much an economic as an environmental decision
Cellulosic
Feedstocks
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Biopolymers are here to stay . . .
• Meet a strategic need to shed our oil addiction
• Meet a strategic need to lower our carbon footprint
• Meet global consumer expectation for sustainability without sacrifice
Biopolymers are no longer “embryonic” (Translation: hard to get, hard to use, very expensive)
Let the journey continue . . .
• New entries into the market place (partially Bio PET, Bio PE, PHA)
• Feedstock diversification
• Economies of scale (resin, converters)
• Recycling infrastructure
Keeping innovation going
Broadening Products
& Applications
Globalizing the
Manufacturing Platform
Monetizing the EOL
Value Proposition
Cellulosic
Feedstocks
Summarizing Comments:
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Acknowledgements:
-Dr. Jeff Kolstad
-Steve Davies
-Andrea Ziadi
-Lisa Moore
-Julie Sobon
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Thank you!
www.natureworksllc.com