based Polycarbonate Polyols for Cast Urethanes

Transcription

CATALYZING GREEN CHEMISTRY
Novel CO2-‐based Polycarbonate Polyols for Cast Urethanes Polyurethane Manufacturers Associa3on May 7, 2013 Las Vegas © 2013 Novomer Inc.
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Who is NOVOMER? §  New Sustainable Chemistry Company – proprietary catalysts to synthe0cally convert CO2 and CO into useful chemicals and materials §  Company History and Overview: §  Founded in 2004 by Geoffrey Coates & ScoA Allen (Cornell University) §  $30 MM in private financing + $21 MM in US DOE funding since 2007 §  Three loca0ons: Ithaca, NY (1400+ m3 lab); Rochester, NY (R&D and scale up); Waltham, MA (Corporate office) §  Mul0ple contract R&D and manufacturing partners §  16 issued and 100+ pending patents on catalysts, manufacturing processes, finished products and select applica0ons © 2013 Novomer Inc.
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High performance polycarbonate polyols from CO2 Novomer’s Technology Precise Polycarbonate Polyols Tradi3onal Chemical Feedstock High Performance • Excep0onal strength • Inherent adhesion to most substrates • Environmental resistance Compe33ve Cost • Raw material cost advantage – 43-‐50% of finished polyol is CO2 • Highly efficient & scalable cataly0c chemistry Standard epoxides (e.g., propylene oxide, ethylene oxide) Renewable / Recycled Feedstock CO2 Clear Sustainability Advantages • 3-‐8x advantage vs. tradi0onal resins • Consistent & transparent LCA; no food vs. materials conflicts Proprietary Novomer Catalyst © 2013 Novomer Inc.
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Novomer’s key innova3on is its unique catalyst for CO2-‐epoxide reac3ons •  Efficient – grams of catalyst produce kilograms of polymer •  Precise – perfect polycarbonate backbone, zero ether linkages •  Robust – uses standard grades of CO2 and epoxides & is shelf stable •  Cost effec0ve – straighhorward to synthesize, recyclable CO2-‐based polyols commercially viable for the first 3me © 2013 Novomer Inc.
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First CO2-‐based Polyol: Polypropylene Carbonate Propylene Oxide (PO) O
Polypropylene Carbonate (PPC) CO2 43% weight CO2 NOVOMER catalyst Direct incorpora3on of CO2 © 2013 Novomer Inc.
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CO2 offers a significant raw material cost advantage… Raw material cost comparison: PPC vs. polyether polyol 50% 25% 0% 3000 MW
PPG Polyol
PO Raw
Material
Savings
CO2 and
Catalyst
Costs
CO2 & Cat. •  20-‐30% raw material cost advantage Propylene Oxide 75% Propylene Oxide 100% •  Similar opera3ng and capital costs at commercial scale Novomer
PPC
Assumptions: 100 MM lb/year capacity, PO at $2000/ton, Depreciation+ROI=25% of CapEx, single use of Novomer catalyst
Source: Nexant Polyether Polyols report, Novomer cost models
© 2013 Novomer Inc.
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… as well as an improved carbon footprint vs. exis3ng petroleum-‐based polyols Novomer CO2 footprint vs. petroleum-‐based polyols and other thermosets 8+ Kg CO2 eq / Kg product 3x to 8x LCA advantage Epoxy Acrylic Polyester Polyol Source: Novomer cradle-‐to-‐gate LCA conducted by DeloiAe Consul0ng / Clear Carbon © 2013 Novomer Inc.
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Polyether Polyol Novomer PPC CATALYZING GREEN CHEMISTRY
In addi3on, use of CO2 avoids the land use and food vs. materials issues associated with NOPs CO2 footprint for Natural Oil and Novomer Polyols Stanford TX, Irrigated NIST TX, Rain Source: Dow LCA Expert Group Presenta0on (2010), Stanford Soy Biohybrid Foam LCA Report (2010) Note: NIST = Na0onal Ins0tute of Standards & Technology © 2013 Novomer Inc.
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Key characteris3cs of CO2-‐based polyols •  100% polycarbonate backbone: perfectly alternating CO2 / epoxide units
yielding 100% carbonate and zero ether linkages
•  Precise control of molecular weight: any Mw from ~500 g/mol to 10,000+
g/mol, all with polydispersity indexes (PDIs) of <1.2
•  Linear or branched: linear 2-functional diols or branched structures can be
created (demonstrated up to 6-fn to date)
•  Perfect -OH functionality: diols are 2.0 functional with zero unsaturation;
hydroxyls can be primary or secondary depending on epoxide used
•  No Color: “Water white” polyols create transparent PU products
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Novomer PPC Polyols (1 of 2) © 2013 Novomer Inc.
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Novomer PPC Polyols (2 of 2) •  Viscous liquids / sob solids at room temp •  Easily processable at elevated temperature (50-‐80 C) •  Compa3ble with tradi3onal ether or ester polyols © 2013 Novomer Inc.
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Understanding the Structure-‐Property Rela3onship of PPC Polyols in Urethanes Novomer has a highly unique polyol technology… Exis3ng Polyol Technology Intui3on on how Novomer might compare Polyethers (PPG, PTMEG) •  Lack of ethers = beAer UV resistance? Polyesters (adipates, etc.) •  Lack of esters = beAer hydroly0c stability? Exis3ng Polycarbonates •  Higher density of carbonate linkages = even higher strength? © 2013 Novomer Inc.
...Thus we looked at its performance in PUs in a two-‐phase approach 1 Study linear PUs changing only polyol (i.e., sob) segment •  PPC vs. exis0ng PCD and ester control polyols •  Same hard segment concentra0on 2 Study how adding PPC impacts exis3ng formula3ons •  Studied both ester-‐based elastomers and ether-‐based foams •  Look for impact of PPC 12
1 CATALYZING GREEN CHEMISTRY
Novomer PPC vs. conven3onal carbonate and ester polyols Hydroxyl Number mg KOH/g Polydispersity Index Mw / Mn 0 125 Viscosity Cen0poise, 70 deg C 250 375 © 2013 Novomer Inc.
500 0 500 1000 13
Existing polycarbonate polyol
Polyester polyol
Acid Value mg KOH/g 1 2 3 4 5 6 7 8 Moisture ppm Novomer PPC
0.0 0.1 0.2 0.3 0.4 Glass Transi3on Temp deg C 1500 -‐40 -‐30 -‐20 -‐10 0 1 CATALYZING GREEN CHEMISTRY
PPC-‐based urethanes have superior hardness and tensile strength Hardness Tensile Strength at Break PPC PC-‐OL PES-‐OL PPC Tes3ng Note: Hardness tested per ASTM D-‐2240, Tensile Strength tested per ASTM D-‐412 © 2013 Novomer Inc.
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Novomer PPC
Existing polycarbonate polyol
Polyester polyol
PC-‐OL PES-‐OL 1 CATALYZING GREEN CHEMISTRY
PPC retains its tensile strength across temperatures beger than exis3ng polycarbonates Tensile Strength at Yield Tes3ng Note: Tensile Strength tested per ASTM D-‐412 at two different temperatures © 2013 Novomer Inc.
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Flexural proper3es of PPC-‐based urethanes were also improved vs. baselines Flexural Strength (kpsi) PPC PC-OL
PES-OL
Flexural Modulus (psi) PC-‐OL PES-‐OL PPC Tes3ng Note: Flexural Strength & Modulus tested per ASTM D-‐790 © 2013 Novomer Inc.
PPC
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PC-‐OL PES-‐OL 1 CATALYZING GREEN CHEMISTRY
PPC-‐based PUs retain their physical proper3es aber exposure to various environments Tensile strength reten3on of PPC-‐based PU test plaques aber 7 days of exposure Excellent resistance to oil, acids, bases, oxida3on, water, ethanol, non-‐polar solvents Low resistance to polar apro3c solvents H2O2 Formula3on Note: Linear PU test plaques made via a pre-‐polymer step with based on 4,4 MDI and PPC at 50% hard segment concentra0on with BDO as a chain extender Tes3ng Note: All samples were submerged for 7 days at room temp except H202, which was changed regularly for 2 wks © 2013 Novomer Inc.
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A wide range of urethanes can be formulated based on PPC polyols (1/4) Tensile at Yield (psi) Lap Shear (psi) Elonga3on (%) Hard + Strong Strong w elas3city Elas3c w strength 100% PPC yields a high strength urethane with low elonga3on (similar to toughened epoxy) Highly elas3c Formula3on Note: PPC concentra0on varies from 20 to 100% by weight; polyester polyol and 4,4 MDI are other components © 2013 Novomer Inc.
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A wide range of urethanes can be formulated based on PPC polyols (2/4) Tensile at Yield (psi) Lap Shear (psi) Elonga3on (%) Hard + Strong Strong w elas3city Elas3c w strength Highly elas3c Blend of PPC and ester polyols yields balance of strength & elonga3on Formula3on Note: PPC concentra0on varies from 20 to 100% by weight; polyester polyol and 4,4 MDI are other components © 2013 Novomer Inc.
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A wide range of urethanes can be formulated based on PPC polyols (3/4) Tensile at Yield (psi) Lap Shear (psi) Elonga3on (%) Hard + Strong Strong w elas3city Elas3c w strength PPC can deliver value as a strength-‐enhancing component of a high elonga3on urethane Highly elas3c Formula3on Note: PPC concentra0on varies from 20 to 100% by weight; polyester polyol and 4,4 MDI are other components © 2013 Novomer Inc.
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A wide range of urethanes can be formulated based on PPC polyols (4/4) Tensile at Yield (psi) Lap Shear (psi) Elonga3on (%) Hard + Strong Strong w elas3city Elas3c w strength Highly elas3c Formula3on Note: PPC concentra0on varies from 20 to 58% by weight with polyester polyol and 4,4 MDI as other components © 2013 Novomer Inc.
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PPC-‐based urethanes exhibit agrac3ve stress behavior in standard tensile tes3ng 43.4 Stress (MPa) 37.2 31.0 24.8 18.6 12.4 6.2 Time (seconds) Tes3ng Note: ASTM D412 © 2013 Novomer Inc.
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PPC-‐based formulated elastomer systems exhibit high elonga3on and low tensile set… Start 0% © 2013 Novomer Inc.
0:20 325% 0:40 525% 23
0:54 580% 1:01 1:26 15% 2 CATALYZING GREEN CHEMISTRY
… In this case, <5% set 3 minutes aber elastomer is stretched to 600%+ elonga3on 1” + <1/16” © 2013 Novomer Inc.
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Another unique property of PPC-‐based PUs: Transparency Commercially Available Polycarbonate Polyol Novomer PPC Polyol © 2013 Novomer Inc.
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Conclusions Dis3nc3ve Performance – unique polycarbonate backbone expands the performance envelope for cast urethane systems • Increased cohesive strength • Increased “inherent” adhesion to a range of substrates • Enhanced environmental resistance • Ability to create tailored PU systems with a range of proper0es including transparency, high elonga0on, and low tensile set Unique Cost and Sustainability advantages – enabled by use of CO2 as a low cost, renewable waste raw material © 2013 Novomer Inc.
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Thank You – Ques3ons? Wayne Willkomm – [email protected]
Jason Anderson – [email protected]
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based Polycarbonate Polyols for Cast Urethanes

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