Novel Polymeric Materials from Biological Oils Richard C. Larock
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1 Novel Polymeric Materials from Biological Oils Richard C. Larock Department of Chemistry Iowa State University
2 Applications of Soybean Oil Most soybean oil has been used for human food. The most promising new uses of soybean oil may be in non-food uses. Human Food Animal Feed Applications of Soybean Oil 6% 14% 80% Non-food Uses: Soap, lubricants, coatings, paints, etc. Our interest is the conversion of soybean and other natural oils to industrially useful bulk polymers.
3 Advantages of Natural Oils Readily available on a huge scale. Very inexpensive. Soybean oil ~23 cents/lb. Corn oil ~25 cents/lb. Billion Pounds Billion Metric Tons Natural and renewable. High purity. U.S. Soybean Oil Production. Source: USDA Relatively high molecular weight. Can be genetically engineered. Many structurally related natural oils are readily available.
4 Soybean Oil Structure 3 ( 2 ) 7 = ( 2 ) 7 CO ( 2 ) 4 = 2 = ( 2 ) 7 CO = 2 = 2 = ( 2 ) 7 CO 2 2 Oleic acid 22% Linoleic acid 54% Linolenic acid 8%
5 Natural and Conjugated Oils Oil C=C Bonds % Composition Conjugated No. C18:1 C18:2 C18:3 Regular soy oil (SOY) LoSatSoy oil (LSS) Conjugated LSS (CLS) Linseed oil (LIN) Conjugated linseed oil (C 100 or 87 LIN) Tung oil (TUN) no no yes no yes yes a a α-eleostearic acid (9,11,13-octadecatrienoic acid) In SOY and LSS oils In CLS, C 100 LIN, C 87 LIN and TUN oils
6 Conjugation of Natural Oils 3 ( 2 ) 4 H C 2 C C H H C ( 2 ) 7 CO 2 R H 0.1 % [RhCl(C 8 H 14 ) 2 ] % (p- 3 C 6 H 4 ) 3 P. 0.8 % SnCl 2 2H 2 O Ethanol 60 o C, 1 day Conjugated Oil Oil Linseed Walnut Safflower Sunflower Soy Corn Sesame Peanut % Conjugation J. Am. Oil. Chem. Soc. 78, 447 (2001)
7 Our Method: Cationic Polymerization CO 2 CO CO 2 Triglyceride ST DVB. cat. BF 3 OEt 2 (BFE) 25 o C / 12h 60 o C / 12h 110 o C / 24h O O C O O C O C O 2 m n n 2 m 2 Note: small amounts of Norway fish oil ethyl ester (NFO) are added for homogeneity.
8 An Overview of the Soybean Oil Polymers The cationic copolymerization of different soybean oils with various alkene comonomers results in thermoset polymers with a glossy dark brown color. The polymers can be made into various shapes by in situ reaction molding or cutting.
9 Glass Transitions of the Soybean Oil Polymers T g ( o g ( C) oc) SOY45-(ST+DVB)47-(NFO5-BFE3) LSS45-(ST+DVB)47-(NFO5-BFE3) CLS45-(ST+DVB)47-(NFO5-BFE3) ν e (mol/m 3 ) A variety of polymeric materials have been prepared with their glass transition temperatures ranging from 10 to 110 o C.
10 Mechanical Properties of Soybean Oil Polymers CLS45-ST47-DVB00-(NFO5-BFE3) CLS45-ST42-DVB05-(NFO5-BFE3) CLS45-ST37-DVB10-(NFO5-BFE3) CLS45-ST32-DVB15-(NFO5-BFE3) A typical soy oil-based elastomer shows an elongation at break of 300%. Stress (MPa) 10 5 CLS45-ST27-DVB20-(NFO5-BFE3) CLS45-ST00-DVB47-(NFO5-BFE3). A typical soy oil-based ductile plastic shows yielding behavior, followed by strain softening and strain hardening A typical soy oil-based rigid plastic shows an ultimate tensile strength of 43 Mpa. Strain (%)
11 Mechanical Properties of Soybean Oil Polymers Characteristics of soybean oil polymers Polymer Tg ( o C) ν e (mol/m 3 ) T max a ( o C) E b (MPa) σ b c (MPa) ε b d (%) Toughnes s (MPa) Polyethylene (LDPE) Polystyrene CLS45-ST47-DVB00-(NFO5-BFE3) e CLS45-ST32-DVB15-(NFO5-BFE3) f CLS35-ST39-DVB18-(NFO5-BFE3) g SOY45-ST32-DVB15-(NFO5-BFE3) LSS45-ST32-DVB15-(NFO5-BFE3) CLS45-ST32-DVB15-(NFO5-BFE3) a The temperature at the maximum degradation rate b Young's modu lus c Break strength d Elongation at break e A typical elastomer f A ductile plastic g A rigid plastic
12 Unique Properties of Soybean Oil Polymers Damping properties Damping materials are capable of reducing unwanted noise and preventing vibration fatigue failure. Good damping polymeric materials should exhibit a high loss factor (tan δ > 0.3) over a wide temperature range of at least o C.
13 Damping Properties of Soybean Oil Polymers Table. Damping results of soy bioplastics measured by DMA at 1 Hz Polymer Tg ( o C) (tan δ) max (tan δ) rt T at tan δ > 0.3 ( o C) tan δ area TA (K) a PU-based IPN b SOY45-ST42-DVB5-(NFO5-BFE3) SOY45-ST37-DVB10-(NFO5-BFE3) SOY45-ST32-DVB15-(NFO5-BFE3) LSS55-ST25-DVB12-(NFO5-BFE3) LSS45-ST37-DVB10-(NFO5-BFE3) CLS45-ST37-DVB10-(NFO5-BFE3) a The background was corrected. b Data for typical polyurethane damping materials [J. Appl. Polym. Sci. 74, 28 (1999)].
14 Unique Properties of Soybean Oil Polymers Shape Memory Properties Shape memory refers to the ability of certain materials to remember a specific shape, on demand, even after rather severe deformations. Shape memory herein refers to thermally stimulated shape memory.
15 Structure Design of Shape Memory Polymers A bending test for shape memory properties has been employed. The soybean oil polymers should be hard plastics at room temperature (Tg > room temperature ). The soybean oil polymers should behave like good elastomers at temperatures higher than their Tg s (stable chemical crosslinks).
16 Shape Memory Effect of Soybean Oil Polymers Recovery (%) SOY45-ST20-(DVB9-NBD9-DCP9)- (NFO5-BFE3) (SOY22.5-LSS22.5)-ST20-(DVB9- NBD9-DCP9)-(NFO5-BFE3) (SOY15-LSS15-CLS15)-ST20- (DVB9-NBD9-DCP9)-(NFO5-BFE3) Temperature ( o C) Polymer Shape memory results (%) a D FD R SOY45-ST20-(DVB9+NBD9+DCP9)-(NFO5-BFE3) (SOY22.5+LSS22.5)-ST20-(DVB9+NBD9+DCP9)-(NFO5-BFE3) (SOY15+LSS15+CLS15)-ST20-(DVB9+NBD9+DCP9)-(NFO5-BFE3) a D: deformability of the polymer at a temperature higher than T g FD: fixed deformation at room temperature, R: recovery
17 Polymers from Other Vegetable Oils Percentages of reacted oil SUN COR SES PNT TUN LIN WNT SAF OIL45-ST32-DVB15-(NFO5-BFE3) All oils have a triglyceride structure composed primarily of oleic acid, linoleic acid and linolenic acid. Generally, higher unsaturation results in a plastic with higher mechanical properties. C=C bonds per triglyceride
18 Polymers from Other Vegetable Oils Table. Tensile mechanical properties of other natural oil-based plastics Samples E (MPa) σ b (MPa) ε b (%) Toughness (MPa) PNT45-ST32-DVB15-(NFO5-BFE3) SES45-ST32-DVB15-(NFO5-BFE3) COR45-ST32-DVB15-(NFO5-BFE3) SUN45-ST32-DVB15-(NFO5-BFE3) SAF45-ST32-DVB15-(NFO5-BFE3) WNT45-ST32-DVB15-(NFO5-BFE3) LIN45-ST32-DVB15-(NFO5-BFE3) The agricultural oil-based polymers exhibit characteristics ranging from soft to tough plastics. Generally, a higher degree of unsaturation in the oil results in a plastic with higher mechanical properties.
19 Thermal and Mechanical Properties Copolymers T g e a Tan Delta Damping TGA Data (¼C) Extractions (%) (¼C) (mol/cm 3 ) Maximum Capacity T 10 T 50 T max Insoluble Soluble SOY50-DCP42-(NFO5-BFE3) SOY55-DCP37-(NFO5-BFE3) SOY60-DCP32-(NFO5-BFE3) SOY65-DCP27-(NFO5-BFE3) SOY70-DCP22-(NFO5-BFE3) SOY75-DCP17-(NFO5-BFE3) C 100 SOY55-DCP37-(NFO5-BFE3) C 100 SOY60-DCP32-(NFO5-BFE3) C 100 SOY65-DCP27-(NFO5-BFE3) C 100 SOY70-DCP22-(NFO5-BFE3) C 100 SOY75-DCP17-(NFO5-BFE3) C 100 SOY80-DCP12-(NFO5-BFE3)
20 Free Radical Polymerization CO 2 CO 2 CO 2 + CN + + NC Me Me C N N C CN Me Me C 100 LIN or CLS AN 60 o C 12 hrs 70 o C 12 hrs 80 o C 12 hrs 90 o C 12 hrs 110 o C 12 hrs 120 o C 12 hrs DVB O O C AIBN (initiator) O C O O C O 2 2 n 2 n CN 2 2
21 Free Radical Polymerization of Conjugated Linseed Oil Sample T g (ºC) Tan Delta T 10 (ºC) T 50 (ºC) T max (ºC) % Sol % Insol C 100 LIN40-AN54-DVB6-AIBN C 100 LIN45-AN49.5-DVB5.5-AIBN C 100 LIN50-AN45-DVB5-AIBN C 100 LIN55-AN40.5-DVB4.5-AIBN C 100 LIN60-AN36-DVB4-AIBN
22 Free Radical Polymerization of Conjugated Soybean Oil Sample T g (ºC) Tan Delta T 10 (ºC) T 50 (ºC) T max (ºC) % Sol % Insol CLS40-AN54-DVB6-AIBN CLS50-AN45-DVB5-AIBN CLS60-AN36-DVB4-AIBN CLS70-AN27-DVB3-AIBN Sample T g (ºC) Tan Delta T 10 (ºC) T 50 (ºC) T max (ºC) % Sol % Insol CLS40-AN54-DCP6-AIBN CLS50-AN45-DCP5-AIBN CLS60-AN36-DCP4-AIBN CLS70-AN27-DCP3-AIBN DCP = dicyclopentadiene
23 Thermal Polymerization of Conjugated Linseed Oil Copolymer Composition T g e E a b b b c Toughness (¼C) (10 4 mol/m 3 ) (Mpa) (Mpa) (%) (Mpa) (C 87 LIN30-ST28-DVB42) hump & (C 87 LIN40-ST24-DVB36) -50 & (C 87 LIN50-ST20-DVB30) -49 & (C 87 LIN60-ST12-DVB28) -49 & (C 87 LIN70-ST08-DVB22) -49 & (C 87 LIN50- ST00-DVB50) -49 & hump (C 87 LIN50-ST10-DVB40) -50 & hump (C 87 LIN50-ST20-DVB30) -49 & (C 87 LIN50-ST30-DVB20) -50 & a YoungÕs Modulus in compression. b Ultimate strength in compression. c Elongation at break in compression.
24 Market Opportunity Analysis Omni Tech International, December 15, Polymers ranging from tough elastomers to rigid composites. At least 50% of the raw materials are natural and renewable. Polymerization at relatively low temperature and pressures. Capital-intensive manufacturing process not required. Raw material costs competitive with commercial polymers. Crosslinking and properties can be controlled over a broad range. Polymers have good thermal stability below 200 o C. Polymers have excellent damping and shape memory properties.
25 Future Research Plans Explore additional properties of the bioplastics. Examine their biodegradation. Find a less expensive replacement for DVB. Develop the elastomers. Prepare a wide variety of composites. Examine real life applications. Utilize other comonomers. More work on other natural oils. Explore other polymerization processes.
26 Summary Industrially promising biopolymers ranging from elastomers to rigid plastics have been prepared. These plastics have excellent thermal and mechanical properties, and unique damping and shape memory properties. Considerable work with composites and other comonomers, oils and processes lies ahead.
27 Acknowledgements CO-WORKERS Dr. Mark V. Hanson David W. Marks Jovin Hasjim Dejan D. Andjelkovic Marlen A. Valverde Dr. Fengkui Li Annik Perround Chad M. Pacha Phillip H. Henna Dr. Patit P. Kundu THANKS TO Dr. Jay-Lin Jane Dr. J. Adin Mann Dr. Valerie Sheares Ashby Dr. Joshua U. Otaigbe
28 Acknowledgements FUNDING AGENCIES Iowa Soybean Promotion Board United Soybean Board Iowa Energy Center Consortium for Plant Biotechnology Research Archer Daniels Midland United States Department of Agriculture Illinois-Missouri Biotechnology Alliance ISU Biorenewable Resources Consortium ISU Center for Catalysis ISU Center for Crops Utilization Research
29 ISU Campus
30 Larock Group
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