DuPont BioMaterials: Enzymatic polymerization - A new ... · DuPont Industrial BioSciences...
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Biobased Performance Materials Symposium
15 June 2017, Wageningen, The Netherlands
Session 2
Presentation by: Christian Lenges, DuPont Industrial BioSciences
Title: DuPont BioMaterials: Enzymatic polymerization - A new process
for engineered polysaccharides
Author: Christian Lenges
Contact details:
Christian P. Lenges
DuPont Industrial BioSciences,
200 Powder Mill Road,
Experimental Station E356,
Wilmington 19803, DE,
USA
Curriculum:
Christian Lenges, Business Development for BioMaterials in DuPont Industrial BioSciences,
focused on the development and launch of growth businesses to make industrially important
chemicals and materials from renewable feedstocks. He has experience in a variety of
businesses and functions in DuPont including product & technology development, portfolio
management & venture leadership. He has had leadership roles in DuPont’s efforts in
Biomaterials since 2008 in the Sorona® business, and in the biomaterial ventures driving
towards commercial launch.
Dr. Lenges holds a Diplom Degree from the Heinrich Heine University in Duesseldorf, and a
Ph.D. in Chemistry & Catalysis from the University of North Carolina at Chapel Hill.
Abstract:
DuPont Industrial BioSciences continues to lead the BioMaterials space by advancing the
development of new material platforms with differentiated performance and unique
customer value. Selecting winning project propositions and managing the complex path
from proof of concept demonstration to commercial launch has been key to creating growth
in the biomaterials space. Within this presentation, one program in the development
portfolio will be discussed in more detail.
Polysaccharides are important biopolymers with a wide range of industrial and consumer
product applications. Historically, structural polysaccharides such as cellulose have been the
backbone of early material science for applications in fibers, films and early thermoplastics.
DuPont Industrial Biosciences has developed a family of engineered polysaccharides ranging
in molecular weights, solubility, and polymer architecture. The underlying enzymatic
polymerization process offers the opportunity to design the polymer structure and the
material properties of these new biomaterials.
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. . . . . . . . . DuPont Industrial Biosciences | Name speaker
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NUVOLVE™ - ENGINEERED POLYSACCHARIDES: ENZYMATIC POLYMERIZATION - ENABLED POLYSACCHARIDES & APPLICATIONS June 14, 2017
Christian Lenges – DuPont Industrial BioSciences
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. . .
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7/3/2017
INNOVATIVE
SCIENCE
HIGH
PERFORMANCE
SCALABLE
SUPPLY
ACCESSIBLE &
AFFORDABLE
RENEWABLE
SOURCING
RESPONSIBLE
BIOMATERIALS
RETHINK RENEWABLE PERFORMANCE DuPont Biomaterials takes cues from nature to create
eco-efficient renewable biomaterials that enhance the
performance of everyday products
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ADVANCING THE FUTURE OF INDUSTRY TO SERVE SOCIETY AND SAFEGUARD THE ENVIRONMENT
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DuPont Industrial Biosciences is working to reform the way we produce and consume
Renewable Agricultural
Resources Industrial Scale Conversion
Sustainable, High-
Performance Products
RENEWABLE SOURCES
Bio/chemical
transformation
Bio/chemical
transformation
BIOACTIVES
BIOMATERIALS
BIOFUELS
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We consider a range of important, inter-connected factors
when developing new biomaterials technology
“Sweet spot” for new
technology development
Economics
& Scalable
Supply Chain
Performance
& Consumer
Benefits
Environmental
& Social Impact
Value-in-use
Market
Relevance
and Accept-
ance
Market
innovation
Production
Capability
Economy
of Scale
Cost
Land Use
Farming
& Bio-
diversity LCA Data
End of Life
Treatment
Gen 1 vs.
Gen 2
Feedstock
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2/2017 6
Sources Matter
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THE STORY OF SORONA
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DUPONT INDUSTRIAL BIOSCIENCES: BIOMATERIALS
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A REVOLUTIONARY PARTNERSHIP = FDME BREAKTHROUGH
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THE NEXT BREAKTHROUGH IN BIOMATERIALS: LEARNING FROM NATURE
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Cellulose b(1,4) linkage
Starch α(1,4) linkage
INSPIRED BY NATURE
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Polysaccharides extracted from plants are widely used to provide unique end-use applications
but are limited by processes and raw material source. Nature often produces mixtures.
Xanthan Gum
Alginates Locust Bean Gum
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BIOMATERIAL PLATFORM INSPIRED BY NATURE
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Cellulose and starch are well known building blocks for natural based materials.
Alpha-1,3-glucan is a largely unexplored structural polysaccharide.
Cellulose: beta (1,4) linkage Starch: alpha (1,4) linkage alpha (1,3) linkage
Engineered Polysaccharide
O
OH
OH OH
OO
OH OH
OH
O
N
O
OH
OH OH
O
O
OH OH
OH
O
N
.
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ENGINEERED POLYMERS DIRECTLY FROM SUGAR
Using enzymatic polymerization to create a variety of polymer
structures with unique product features and application benefits
Linkage control: Selective polymerization of sucrose to polysaccharide
Structural control: Crystallinity, solubility – DPW & PDI Control
Process control to define polymer microstructure
POLYMER
CH2OH
H O H
OH
O
H
H
H
OH
O
CH2OH H O
CH2OH
H
O
H
H
OH
SUCROSE BIOCATALYST
PolySaccharide
Applications
Paper Coatings
Fibers & Fiber Additives
Composites
Packaging
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BIOPROCESS CONTROL: FROM MOLECULAR DESIGN TO POLYMER ARCHITECTURE & PARTICLE MORPHOLOGY
Platform Technology to Engineer New Raw Materials
MATERIAL
MORPHOLOGY POLYMER
ARCHITECTURE
Linear vs Branched
Structures
CH2OH
H O H
O
H
O
H
H
H
O
H
O
CH2OH H O
CH2O
H
H
O
H
H
O
H
SUCROSE ENZYMATIC
POLYMERIZATION
MOLECULAR
DESIGN
Linkage Control
Selective Functionalization
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BIOCATALYST – GLUCOSYLTRANSFERASE (GTF)
Highly conserved structure despite significant sequence diversity
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Signal peptide
Catalytic domain Glucan binding
domain
Variable
domain
GTF from S. mutans
NCBI database
Glycoside-Hydrolase family 70 (GH70)
Monomer with typical MW of 160 kDa
Extracellular enzymes, mainly produced by:
Streptococcus species
Leuconostoc species
Lactobacillus species
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NUVOLVE™ ENGINEERED POLYSACCHARIDES PATH TO COMMERCIAL REALITY
Key Status Highlights
• Advancing process, product & application development
• Targeting first commercial scale supply
• Ongoing pilot plant operations to supply first sales
• Development materials available
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POLYSACCHARIDE BASIC PROPERTIES – ALPHA 1,3-GLUCAN
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Typical Properties
Brightness 90 - 96
Degree of Polymerization 800 (400 – 1500)
PDI 1.7 - 2
Residual Sugars 0.1-1.0 wt%
Dry polymer solids > 88 wt%
Particle size distribution (d50) 10-30 µm
Primary Particle Size 10 – 30 nm
Overall Surface Energy 53 mJ/m2
Crystallinity Index ~ 50%
Bulk Density 1.5 kg/m3
o Water insoluble free flowing powder
o Zeta Potential essentially zero !
o Water absorption isotherm between cellulose I & II
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BIODEGRADABILITY ASSESSMENTS
ASTM D5511: simulates & accelerates biodegradation
process in landfill
Final biodegradation was 85% +/-1.0% or 105.0% relative
to reference cellulose
Conclusion: Considered completely biodegradable under
mesophilic anaerobic conditions.
High Solid Anaerobic Degradation
Under Mesophilic Conditions (37C)
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Soil Biodegradation Test
ISO 17556 Plastics: determines ultimate aerobic
biodegradability in soil
Final biodegradation was 85.6% +/- 0.3% or 104.4%
relative to reference cellulose
Conclusion: Fulfilled 90% requirement within 90 days of
testing under given aerobic conditions.
OWS
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POLYSACCHARIDE IN BIOCOMPOSITE APPLICATION EXAMPLES
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Engineered polysaccharides from DuPont show promising performance
results across multiple markets & applications. For example:
RUBBER COMPOSITES
THERMOPLASTIC COMPOSITES
HIGH SPEED INK JET COATINGS
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THERMOPLASTIC FILLER APPLICATIONS
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Spherical Particle in Powder Form (5-10 micron)
Efficiently Compounded into PP, PE, PLA, others
Maintains Mechanical Properties of Compounds
at high PolySaccharide load
Example 10% - 40% additive in PLA:
Tensile Modulus: 4000 +/- 500 [MPa]
Tensile Strength: 40 +/- 10 [MPa]
Whiteness & Low impurities
Thermal Stability
Less degradation byproducts
Low melt viscosity - even at high loads
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PLA / POLYSACCHARIDE COMPOUNDS
Target Injection Molding and Extrusion Grades
Assessment of Coupling Additives to Improve Thermal Stability
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Poly-
Saccharide %
Coupling
Additive
Yield
stress
(Mpa)
Notched
Izod (J/M)
Elongation
% HDT (C) Biocontent
0 - 50 27 <5 55-100 100%
20 - 55 35 5 - 8 67 100%
20 A 52 32 5 130 98%
30 A 48 32 5 130 98%
20 B 45 27 4.5 140 96%
20 C 45 41 15 140 90%
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PLA / POLYSACCHARIDE COMPOUNDS: BIODEGRADABILITY SYNERGIES
PolySaccharides Meet fundamental Biodegradability
Requirements across key certification categories
PLA/PolySaccharide Compounds with Synergistic Effect
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Engineered PolySaccharides
in biobased thermoplastics
Meeting biodegradability targets at high bio content
Improved performance Modulus, HDT, Color
Processability injection cycle time & throughput
06/May/2017
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TEM Images of Glucan polymer from Enzymatic Polymerization BioProcess: Primary Particle
BIOPROCESS CONTROL: FROM MOLECULAR DESIGN TO POLYMER ARCHITECTURE & PARTICLE MORPHOLOGY
CH2OH H O H
O
H
O
H
H
H
O
H
O
CH2OH H O
CH2O
H
H
O
H
H
O
H
SUCROSE PRIMARY
PARTICLE
ENZYMATIC
POLYMERIZATION AGGLOMERATES PARTICLE
AGGREGATES
Associated Glucan Chains 10-30 nm 100-300 nm 1000-5000 nm
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Key Requirements:
Compatibility with Rubber Formulations
Maintain or Improve Properties
Advancing Sustainability & Performance
Rubber/Filler Processing
Base Line Composites Results
Examples: Carbon Black & Silica Replacement
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Rubber
Filler
Reinforcing Materials
Plasticizers, Anti-ageing
Vulcanization Additives
Adopt to
Current Process
Compound
Processing
Rubber Raw
Materials
Match &
Advance on
Performance
End
Use
Markets
Tires
Belts
Hoses, Gaskets
Shoes etc
Curing
Process
Product
Forming Processes
NUVOLVE™ ENGINEERED POLYSACCHARIDES: REINFORCING FILLER APPLICATION OPPORTUNITIES
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ASSESSMENT IN TYPICAL RUBBER PROCESSING: COMPOUND DEVELOPMENT
Replace carbon black and/or silicas at various levels
Current coupling agents viable
Good wetting, homogenous, non-porous
Lower torque – Decrease in viscosity
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TEM images displays the dispersion polysaccharide – silica hybrid
reinforcing fillers in rubber compounds
- Effective dispersion in rubber composite
- No significant agglomeration of polysaccharide particles observed
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EXAMPLE: CARBON BLACK REPLACEMENT IN TIRE TREAD FORMULATIONS
Improvement of elongation & overall toughness
Tan delta (60C) of composites has improved
Rebound: increased at RT & decreased at 0°C
Lower density – 10-20%
Different grades of polysaccharide fillers
Surface area change
Lower particle size / higher surface activity
Improve abrasion / maintain Tan delta (60C)
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Compound Compatibility & Positive Impact on Dynamic Performance
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PTS MUNICH LAB-HIGH SPEED INKJET – PRINTER TEST UNIT
7/3/2017
The printing system is equipped with two
Industrial Oce/Canon print heads (piezo), and a wipe unit
Inks: pigment ink Oce black and cyan
Printing speed: up to 100 m/min
Wiping of 3 Data Matrix Codes after predefined drying time 1,7 seconds
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HSI Not wiped HSI Wiped
(1,7 s) Desk Jet
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GLUCAN CAN MAKE A SIMPLE COATED PAPER INK JET PRINTABLE
parameters Control
S4-HSI3 S4-HSI3.1
Coating Formulations
UF CaCO3 – 100
Starch - 15
UF CaCO3 – 70
Starch – 15
Glucan - 30
coating weight g/m² 8,1 8,3
coating thickness µm 5,4 7
printing test with HSI printer
wipe-test
after 1,7 sec 600 dpi A/F A/A
non wiped/wiped 900 dpi A/- A/C
1200 dpi A/- B/F
Printing Test with Desk Top Printer
Color Density Power Spectrum
Black/ Cyan
22.6
90
25.8
93.2
Mottle Index Power Spectrum
Black/Cyan
10.3
32.7
9.8
15
Less „smear“ due to faster ink absorption.
Better color density, dot gain and mottle
index.
HSI3
Reference
Glucan HSI 3
7/3/2017 29
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HIGH SPEED INKJET – SEM HSI 3 (X 3000)
HSI 3 100 parts UF CaCO3 HSI 3.1 30 parts PSCC, 70 parts UF CaCO3
Polysaccharide Increases Porosity of Coating Enhancing Water Absorption
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NO LOSS IN QUALITY - REDUCTION IN SILICA AND BINDERS IN HIGH QUALITY IJ COATING
parameters Control S1-HSI1.4
Coating Formulations
Silica 1 – 75
Silica 2 - 18
--------------
PVOH – 34
PVAc – 50
Others - 17
Silica 1 – 50
Silica 2 – 18
Glucan – 25
------------------
PVOH – 34
PVAc – 40
Others -17
coating weight g/m² 6.1 6.2
coating thickness µm 18.3 19.1
printing test with HSI printer
wipe-test
after 1,7 sec 600 dpi A/A A/A
non wiped/wiped 900 dpi A/A A/A
1200 dpi A/F A/F
Printing Test with Desk Top Printer
Color Density Power Spectrum
Black/ Cyan
34.5
90
35.1
92.3
Mottle Index Power Spectrum
Black/Cyan
0.6
1.2
0.8
1.9
7/3/2017 31
Control Replace 25 parts Si
With Glucan
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NUVOLVE™ ENGINEERED POLYSACCHARIDES THROUGH ENZYMATIC POLYMERIZATION
New Class of Renewable
Material with Unique Properties
Key Processing Benefits
Rapidly Renewable, Regional
Feedstock
LCA, Land Use, Light Weighing
& Reduced Fuel Consumption
Advancing to Commercial
Reality
Multi ton quantities available for
Development
.
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THANK YOU FOR YOUR ATTENTION
Learn more about DuPont Biomaterials
33
7/20/16
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@DuPontBiobased
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