DuPont™ Cerenol™ A New Family of Sustainable and Environmentally Friendly Materials The 12th Annual Green Chemistry and Engineering Conference June 24-26, 2008, Washington DC Hari B Sunkara DuPont Central & Research Development
Agenda Introduction DuPont™ Cerenol™ Cerenol™ vs Commercial Polyols DuPont sustainability goals PDO based polymers and products DuPont™ Cerenol™ Products, processes and properties Cerenol™ vs Commercial Polyols Cerenol™ Based Products Hytrel® RS Thermoplastic Elastomers Performance Coatings
Sustainable Growth Trends Growth in developing countries Increased food production Renewable energy and materials Greater safety and security Increased connectivity
DuPont 2015 Sustainability Goals Marketplace goals Double R&D investment in environmentally smart market opportunities. Grow annual revenue $2 billion or more from products that create energy-efficiency and/or reduce greenhouse gas emissions. Double annual revenue to $8 billion from non-depletable resources. Introduce at least 1,000 new safety products or services.
DuPont Tate and Lyle Bio PDO™ manufacturing facility DuPont Applied BioSciences uses science to bring breakthrough biotechnology-based products to the world. DuPont Tate and Lyle Bio PDO™ manufacturing facility Businesses BioMaterials BioFuels BioSpecialties BioMedical Key Products PDO-based polymers and products Biobutanol/Cellulosic ethanol Peptides Medical adhesives & embolics Omega-3 fatty acids
Examples of final product brands Bio-PDO™ serves as a building block for diverse applications and markets Ingredient Brand Markets Examples of final product brands Textile Fibers Smartstrand Carpet Fibers Resins, Films, etc. Bio-PDO™ Zemea™ Susterra™ Direct Applications Specialty Applications Elastomers Stretch Fibers Zemea™ & SusterraTM are registered trademarks of the DuPont Tate & Lyle Bio Products Company
Agenda Introduction DuPont™ Cerenol™ Cerenol™ vs Commercial Polyols DuPont sustainability goals PDO based polymers and products DuPont™ Cerenol™ Products, processes and properties Cerenol™ vs Commercial Polyols Cerenol™ Based Products Hytrel® RS Thermoplastic Elastomers Performance Coatings
[ ] Cerenol™ is a family of high performance renewably sourced polyols Biomass Feed Stock Bio-PDO™ Cerenol™ Zemea™ Susterra™ Products Structure Bio Content Homopolymer (H-Series) 100% Copolyetherglycol (G-Series) 70-80% Polyetherglycol ester (E-Series) 50-60% O C [ ] OH H n O C [ H ] OH ROC O COR n
Cerenol™ uses an environmentally Friendly Process Cerenol™ batch manufacturing facility Process benefits Renewably sourced ingredient One step polycondensation process Safer manufacturing process Less energy consumption Less GHG emission Low toxic product Inherent Biodegradability
Cerenol™ Commercial Homopolymers Typical Property Ranges Property Cerenol H650 H1000 H1400 H2000 H2400 Molecular weight 600 - 700 900 - 1100 1300 - 1450 1900- 2100 2300 - 2500 Hydroxl number 187.0 - 160.3 124.7 -102.0 86.3 - 77.4 59.1 - 53.4 48.8 - 44.9 Unsaturation, meq/g 0.02 max OH Functionality ~2 Alkalinity, meq/30 kg -2.0 - 2.0 -2.0 - 2.0 Color, APHA 50 max Melting point (Tm), oC 9 - 11 12 - 14 15 - 17 16 - 18 17 - 19 Density @ 40 oC, g/cc 1.019 1.018 1.017 1.016 Viscosity @40 oC, cP 100 - 150 190 - 260 310 - 420 720 - 850 950 - 1100
Cerenol™ has led to multiple inventions on products, processes and uses Filed applications on product, process and applications Filed applications by market Specialty polymers Functional fluids Product & Processes Product Applications Coatings & Inks Personal care Fibers >90 US Patent Applications Filed 60 Granted/Published
Agenda Introduction DuPont™ Cerenol™ Cerenol™ vs Commercial Polyols DuPont sustainability goals PDO based polymers and products DuPont™ Cerenol™ Products, processes and properties Cerenol™ vs Commercial Polyols Cerenol™ Based Products Hytrel® RS Thermoplastic Elastomers Performance Coatings
Cerenol™ compares best to high performance polyether diols Petroleum Based Synthetic Polyether Diols Polyethylene glycol (PEG) Polypropylene glycol (PPG) Polyethylene-propylene glycols (EO/PO) Polytetramethylene ether glycol (PTMEG) Vegetable Oil based Polyols (Oleochemical Polyols) Soy bean oil based polyols Castor oil
Cerenol™ is an ideal soft segment for thermoplastic elastomers Properties of Cerenol™ vs. other Polyols
Cerenol™ is relatively amorphous and easy processable polyol Properties of Cerenol™ vs Fossil fuel based Polyols
Universal V4.2E TA Instruments Cerenol™ has comparable Thermo-oxidative stability vs. PTMEG in spite the higher ether links Cerenol™ vs PTMEG 16.00min 99.12% 59.01min 50.00% 92.24min 20.00% 97.99% 58.54min 92.12min 20 40 60 80 100 120 Weight (%) 140 160 180 200 Time (min) PTMEG 1400 ––––––– Cerenol 1400 Universal V4.2E TA Instruments Isothermal at 175 oC in air
Cerenol™ is an excellent ingredient for both thermoset and thermoplastic polymers Properties of Cerenol™ vs. Biobased polyols Typical Properties Cerenol™ H2000 Biobased Polyol Molecular weight 2010 1700 1100 Hydroxyl number, mg KOH/g 56 235 Hydroxyl type Primary Secondary OH Functionality 2 2 (average) 4.4 (average) Viscosity @ 25 oC, cP 1840 4500 8900 Density, g/mL 1.02 (40 oC) 1.00 1.01 Color 50 APHA (Max) < 1 G < 2 G Flash point, oC > 230 > 130 >130 Acid value, mg KOH/g 0.003 0.30 1.7 Water, ppm <500 500 3000
Greenhouse Gas Emissions Cerenol™ reduces the environmental footprint vs. PTMEG (cradle to gate life cycle analysis) Fossil Energy Greenhouse Gas Emissions 40% 3 (Industry average4) 3 42% (Industry average4) 1Industry Average: 39% Reppe, 26% GEMINOX, 21% Davy, 14% Mitsubishi
Agenda Introduction DuPont™ Cerenol™ Cerenol™ vs. Commercial Polyols DuPont sustainability goals PDO based polymers and products DuPont™ Cerenol™ Products, processes and properties Cerenol™ vs. Commercial Polyols Cerenol™ Based Products Hytrel® RS Thermoplastic Elastomers Performance Coatings
Cerenol™ Based Products from DuPont DuPont™ Hytrel® RS Thermoplastic Elastomer 25-60% Renewable content Comparable performance to standard grades of Hytrel® Performance Coatings for new automotive primers and clearcoats Cerenol™ is used as an additive Improved flexibility and chip resistance Imron® polyurethane enamels Superior durability, gloss and color retention --
Cerenol™ is more compatible with PBT Hard segment than PTMEG CLEAR MELT 60 PTMEG Soft segment content (%wt) 40 Cerenol™ 20 PHASED MELT 1000 1500 2000 2500 Polyether Polyol Mn (g/mol)
Cerenol™ enhances performance of COPE resins Standard Renewable Less Stiffness at - 40oC Improved elastic recovery
Cerenol™ vs. PTMEG-COPE Aging Performance HEAT UV OIL Cerenol™ Sample PTMEG Sample Changing from PTMEG to Cerenol™ as a soft segment does not impact aging despite the increase in ether linkages
Durability of Clear coats Cerenol™ in Performance Coatings (US Patents: 6,875,514; 7,169,475; 7,268,182) Improvement in chip resistance Improvement in flexibility Hardness retention Durability of Clear coats 4+ years of Florida exposure Comparable or better retention of gloss and DOI Cerenol™ formulation Control
Cerenol™ in Performance Coatings Adhesion Improvement Decrease in coating dry time
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