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Methylene Malonates & Cyanoacrylates
Energy Efficient, High Performance Sustainable Adhesive Systems
Matt Ellison Director of Reactive Technology
Bioformix, Inc.
International Conference on Wood Adhesives 2013 October 11, 2013
Bioformix, Inc. Copyright 2013
Outline
• Value Proposition • Millwork Assembly Opportunities
• Potential Wood Composite Assembly Advances
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Bioformix, Inc. Copyright 2013
Bioformix Overview"Building a Disruptive Specialty Chemicals Company "
Company Description § Eliminates energy and solvents - vastly cuts customer costs § Significantly increases production speeds with high speed curing § Benign by design – plastics can be metabolically benign § Transforms adhesives, coatings and composites manufacturing § Developed broad classes of monomers and polymers from one chemistry § Commercial and NRE revenue today
Management Team § Veteran management, technical, and sales team, 28 yrs avg experience § Leadership roles in major specialty chemical companies § Experience from Loctite, Henkel, 3M, HB Fuller § Successful start-up experience – Nexicor, Nature Seal, Closure Medical § Deep, personal relationships with many customers
Investment Thesis § Platform technology with numerous applications across $150B+ markets § Enables disruptive reduction of energy consumption in manufacturing § Capital light model – leveraged partnerships via strong IP
Commercialization Strategy § Scaling up production capacity with partners for speed to market § Initially pursuing high margin (70%+) reactive products platform § Near-term: adhesives, coatings, composites & inks - $30B+ market § Longer-term: work with partners to pursue $120B+ commodity markets
High Performance, Energy Efficient, Sustainable Polymer Platforms
Company HQ:
Year Founded:
Company Summary
Market Opportunity:
Technology:
Cincinnati, OH
2009
Specialty chemicals Initially 9 major markets Initial markets - $150B
Breakthrough monomers will be building blocks for whole new class of specialty chemicals
Investors:
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Bioformix, Inc. Copyright 2013
Unique Approach to Green Chemistry " Value is delivered in performance & operational costs "
Category Current “Green” Bioformix “Green”
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Enabling significant reduction of industrial energy consumption
Dramatically improving product performance
Replacing undesirable materials Green is nice, but value is in performance!
Bioformix, Inc. Copyright 2013
Unique Approach to Green Chemistry Bioformix provides low-capex solutions that solve customer problems"
Category Current “Green” Bioformix
Value Add
Volume
Platform & Markets
Capex
Supply Chain
§ Generally commodity product § No value add beyond “green”
§ Generally commodity markets § Capital efficiency? § Low margin, high investment
§ Generally single products § Bio platforms & new unit ops § Significant, long development
§ Low margins and large volumes § Large capex, large scale-up § Long, expensive path to market
§ New supply chains not scaled § Sugar / cellulosic biomass
§ Powerfully added value § Energy saved, fast manufacturing § Improved performance, green
§ Low volume, high value focus § Low performance applications § High prices, low investment
§ 100s of monomers § Make an infinite plastics menu § Broad, enabling, practical
§ Low initial volumes, low purity § Min investment, short time to mkt § Producing low-volume today
§ Existing petro supply chain § Switch to green supply later § CO, CO2, Methane & Sugars
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Bioformix, Inc. Copyright 2013
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Potential Millwork Opportunities
Applying trim – Cyanoacrylate and Malonate
Bonding center panels – Cyanoacrylate and Malonate
Assembling drawer boxes – Cyanoacrylate and Malonate
Assembling door frames – Cyanoacrylate and Malonate
Manufacturing plywood for cabinet boxes – Malonate
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New CAs Equal or Better Incumbents
0
1
2
3
4
5
6
7
8 Strength
Ease of Use
Odor Environmental
Resistance
Cure Speed
Improved CAs
PVA Emulsion
Liquid Urethanes
Epoxies
Hot Melt
1 – Poorer 8 - Better
Bioformix, Inc. Copyright 2013
Cabinet Door Assembly Model
Adhesive Application
Clamp Time Cure Time
Current State • Manual
Improved CA • Automated
Door Frame
Current State • Pinned
Improved CA • No Pinning
Door Panel
Current Door Panel • ~45 minutes
Improved CA • Minutes
Door Frame
Current State • Varied
Improved CA • Minutes
Door Panel
Current Door Panel • 10-15 hours
Improved CA • Minutes
Bioformix, Inc. Copyright 2013
Cure Speed Effect
Bioformix, Inc. Copyright 2013
Tensile Strength Comparison
Nexabond™ Short
Nexabond™ Medium
Nexabond™ Long
PVA emulsion
Competitive CA with Activator
Bioformix, Inc. Copyright 2013
Nexabond Adhesive Water Resistance
1 hr RT soak 2 hr bake 121C Return to water when hot 3 cycles Followed by testing dry
Bioformix, Inc. Copyright 2013
Tech Platform: Methylene Malonates A core platform monomer 130 years in the making… "
§ Polymer platform out performs most others - Discovery of methylene malonates dates back to 1877, but no one
was ever able to make stable - Bioformix developed a proprietary production process to produce
stable methylene malonates - Benign by design – can be metabolically and bio compatible
§ Sponsoring Applications: Adhesives & Coatings - Combines super glue’s ambient, fast cure with epoxy performance
§ Initial capacity of three million pounds per year - By the first quarter of 2014 or earlier - Development partner Shepherd Chemical hosting production - Continuous process pilot scale-up completed except distillation
§ Many monomers = Infinite array of polymers
§ Filed broad patent protection – 12+ applications - Critical monomer & resin process breakthroughs accomplished - Major key applications and modes of use protected - Not just the products, but the devices to produce and/or use them
Key Product Advantages
§ Super glue cure speeds § Epoxy performance
§ Survives high temperatures
§ Solvent resistant, including water
§ One part, no mixing
§ No heat for curing § No odor
§ Non flammable
§ Biologically benign & biodegradable
§ Can replace BPA, other dangers
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Platform Structure Features Benefits
Methylene Malonates
(MMs)
High speed polymerization Zero energy polymerization Highly variable structures Powerful solvent resistance Strong thermal resistance
High Speed Manufacturing Energy efficiency Long product life New materials
Methylene Acetyl Acetonates
Same as Methylene Malonates plus... Controlled resin structures Stronger thermal resistance
Same as MMs plus... Harsher Environments
Methylene Beta-Diketones
Same as MMs plus... Strongest Resistance
Same as MMs plus... Longest Life
O
O
R2
O
R1
O
CH2
O
R2
O
R1
O
CH2
O
R2
O
R1
CH2
Multiple Monomer Platforms Near infinite variety of options
Bioformix, Inc. Copyright 2013
Malonate Thermal Resistance
0
20
40
60
80
100
120
0 10 20 30 40 50 60 70 80
Per
cent
age
of
Init
ial S
hear
Str
eng
th (%
)
Hours at 121ºC
Crosslinked Malonate
Diethyl methylene malonate
Ethyl Cyanoacrylate
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Malonates Can Outperform Competition
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1
2
3
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5
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8 Strength
Ease of Use
Odor Environmental
Resistance
Cure Speed
Malonates
Improved CAs
PVA Emulsion
Liquid Urethanes
Epoxies
Hot Melt
1 – Poorer 8 - Better
Bioformix, Inc. Copyright 2013
Fiber, Particle or Sheet Coating with Binders
Automated Cure in a
Press or Fixture
Forming the Parts
Large Scale Application Wood Panel Example (From Millwork/Furniture to Particle Board)
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Bioformix’s monomer drops into existing composite processes
Simply add the monomer into existing applicator and turn off drying ovens
Eliminate production pauses for cure time & eliminate stresses
• High speed • No heat • Water free • Solvent free • Formaldehyde free • Biosafe
Panels cost 20% less
Bioformix, Inc. Copyright 2013
50% Less Capital Costs per Plant, One
Plant
50% Less Energy Costs per Plant
One Plant
Twice the speed or more
Half the plants!
$10,000,000’s annually $50,000,000 plus per plant
CAPEX OPEX
Large Scale Application Composites Example (From Millwork/Furniture to Particle Board)
Today: Two Wood Panel Plants
Bioformix Enabled: One Wood Panel Plant
Instant no energy cure means that the rate limiting step of cure time can be removed – doubling output of each plant; no energy cure cuts opex 50+%
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Bioformix, Inc. Copyright 2013
Design polymers to be biocompatible, biodegradable or metabolizable
polymer many units “Plastic”
metabolizable digested by living things
biodegradable digested by living things
biocompatible tolerated by living things
Green Polymers Biologically Benign by Design
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Conclusions
Improved cyanoacrylates
• increased savings • reduce/eliminate clamping time • minimize effect of humidity/wood type • enable increased throughput
New Methylene malonates offer
• increased savings • reduced manufacturing via instant cure • reduced energy costs through ambient cure • superior performance/exterior use
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Acknowledgments
• Adam Malofsky, Ph. D. • Bernie Malofsky, Ph. D. • Stan Wojciak • Applications Group – Kim Kerns – Joe DeSousa, Ph. D. – Peter Stevenson – Peter Roman
• Analytical Group – Ben Chew, Ph.D. – Susan Russell, Ph. D. – Julie Hess