DuPont Cerenol A New Family of High Performance Polyether glycols

Transcription

1 DuPont Cerenol A New Family of High Performance Polyether glycols Fifth Annual World Congress on Industrial Biotechnology & Bioprocessing April 27-30, 2008, Chicago Hari B Sunkara & Ray W. Miller DuPont CRD/Applied BioSciences

2 Agenda 2 Introduction 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

3 Sustainable Growth Trends 3 Growth in developing countries Increased food production Renewable energy and materials Greater safety and security Increased connectivity

4 DuPont 2015 Sustainability Goals 4 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.

5 5 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 Peptides Medical adhesives & embolics Omega-3 fatty acids

6 Bio-PDO serves as a building block for diverse applications and markets 6 Ingredient Brand Markets Textile Fibers Carpet Fibers Examples of final product brands Smartstrand Bio-PDO Zemea Susterra Resins, Films, etc. Direct Applications Specialty Applications Elastomers Zemea & Susterra TM are registered trademarks of the DuPont Tate & Lyle Bio Products Company Stretch Fibers

7 Agenda 7 Introduction 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

8 Cerenol is a family of high performance renewably sourced polyols 8 Biomass Feed Stock Bio-PDO Zemea Susterra Cerenol Products Structure Bio Content Homopolymer (H-Series) H C C [ O C ] OH n 100% Copolyetherglycol (G-Series) H [ O C C C O C C ] OH 70-80% Polyetherglycol ester (E-Series) ROCO O O OCOR n 50-60%

9 9 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

10 Cerenol Commercial Homopolymers 10 Typical Property Ranges Property Cerenol H650 Cerenol H1000 Cerenol H1400 Cerenol H2000 Cerenol H2400 Molecular weight Hydroxl number Unsaturation, meq/g 0.02 max 0.02 max 0.02 max 0.02 max 0.02 max OH Functionality ~2 ~2 ~2 ~2 ~2 Alkalinity, meq/30 kg Color, APHA 50 max 50 max 50 max 50 max 50 max Melting point (T m ), o C o C, g/cc o C, cp

11 Cerenol has led to multiple inventions on products, processes and uses 11 Filed applications on product, process and applications Filed application by market Specialty polymers Functional fluids Product & Processes Product Applications Coatings & Inks Personal care Fibers 90 US Patent Applications Filed. 58 Granted or Published

12 Agenda 12 Introduction 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

13 Cerenol compares best to high performance polyether diols 13 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

14 Cerenol is an ideal soft segment for thermoplastic elastomers 14 Properties of Cerenol vs. other Polyols Properties PPG Cerenol PTMEG Biobased Polyol Structure Raw material source Non renewable HO-CH 2 -CH 2 -CH 2 -O H n HO-CH 2 -CH 2 -CH 2 -CH 2 O H n Renewable Non renewable Renewable Hydroxyl type Secondary Primary Primary Secondary Reactivity Low High High Low Physical state Liquid Liquid/solid Solid Liquid Crystallinity Amorphous Semi crystalline Semi crystalline Polydispersity Narrow Broad Broad Melting point No melt Low High T g Low Low Low Viscosity Very low Low High High Oxidative stability Inferior Superior Superior Inferior Properties variability CH 3 HO CH 2 -CH- O H CHn 3 Low Low Low High

15 Cerenol is relatively amorphous and easy processable polyol 15 Properties of Cerenol vs Fossil fuel based Polyols Polyol Tg o C Tm o C Viscosity 60 o C cp Tc o C Crystallization half time a minutes MWD PEG ND < 1.2 PTMEG T Cerenol H none a at -5 deg C

16 Cerenol has comparable Thermo-oxidative stability vs. PTMEG in spite the higher ether links Cerenol vs PTMEG TGA in Air PTMEG-1400 Cerenol Isothermal at 175 o C in air PTMEG 1400 Cerenol 1400 % Weight loss in air Weight (%) min 99.12% 16.00min 97.99% 59.01min 50.00% 58.54min 50.00% min 20.00% 92.24min 20.00% Time (min) Universal V4.2E Temperature, C

17 Cerenol is an excellent ingredient for both thermoset and thermoplastic polymers 17 Properties of Cerenol vs. Biobased polyols Typical Properties Cerenol H2000 Biobased Polyol Biobased Polyol Molecular weight Hydroxyl number, mg KOH/g Hydroxyl type Primary Secondary Secondary OH Functionality 2 2 (average) 4.4 (average) 25 o C, cp Density, g/ml 1.02 (40 o C) Color 50 APHA (Max) < 1 G < 2 G Flash point, o C > 230 > 130 >130 Acid value, mg KOH/g Water, ppm <

18 18 Cerenol reduces the environmental footprint vs. PTMEG (cradle to gate life cycle analysis) Greenhouse Gas Emissions Fossil Energy 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% Total Non-Renewable Energy (Fossil + Nuclear) relative to fossil PTMEG industry average, (%) PTMEG CERENOL (Industry average 4 ) 3 40% 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% Greenhouse Gas Emissions (Fossil + Nuclear) relative to fossil PTMEG industry average, (%) PTMEG CERENOL (Industry average 4 ) 3 42% 1 Industry Average: 39% Reppe, 26% GEMINOX, 21% Davy, 14% Mitsubishi

19 Agenda 19 Introduction 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

20 Cerenol Based Products from DuPont 20 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

21 Cerenol is more compatible with PBT Hard segment than PTMEG 21 Soft segment content (%wt) CLEAR MELT PTMEG Cerenol PHASED MELT Polyether Polyol Mn (g/mol)

22 22 Cerenol enhances performance of COPE resins Less Stiffness at - 40 o C Improved elastic recovery E' M o dulus [M P a] Renewable Standard Temperature [ C] Elastic deformation [%] = f (Total deformation) Renewable Measured at 50,100,200 and 300[%] at 23ºC, 50mm/min on 80mm of a Tensile 1BA. Values reported after 1st cycle Total deformation [%] Standard

23 Cerenol vs. PTMEG-TPE Aging Performance % 55D HEAT polymer 45D UV polymer 45D OIL Polymer (NON UV STABILIZED) (LOW HEAT STABILIZER) 100% 100% Retention of Elongation 80% 60% 40% 20% 0% C in air Cerenol Sample Retention of Tensile Strength 80% 60% 40% 20% 0% Days QUV Exposure PTMEG Sample Elongation Retention 80% 60% 40% 20% 0% ºC in ASTM Oil #3 Changing from PTMEG to Cerenol as a soft segment does not impact aging despite the increase in ether linkages

24 24 Cerenol in Performance Coatings (US Patents: 6,875,514; 7,169,475; 27,268,182) Control Cerenol formulation 120% Durability of Clear coats 100% 80% 60% 40% 20% 0% Lab V7500S 3.50% 7% 10.50% V7500S Improvement in chip resistance Improvement in flexibility Hardness retention % 20 Gloss ret. 1 year % 20 Gloss ret. 3 yr %20Gloss ret months %DOI ret. 1 year % DOI ret. 3 year %DOI ret months 4+ years of Florida exposure Comparable or better retention of gloss and DOI

25 Cerenol in Performance Coatings 25 Adhesion Improvement Decrease in coating dry time

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