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(12) United States Patent (10) Patent No.: US 8,097,739 B2 Luo Et Al

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(12) United States Patent (10) Patent No.: US 8,097,739 B2 Luo Et Al USO08097739B2 (12) United States Patent (10) Patent No.: US 8,097,739 B2 Luo et al. (45) Date of Patent: Jan. 17, 2012 (54) PROCESS FOR THE MANUFACTURE OF 2006/0276609 A1* 12/2006 Lysenko et al. ................. 528.44 NATURAL OIL HYDROXYLATES 2007/O123725 A1 5/2007 Lorenz 2007/0173632 A1 7, 2007 Odaka (75) Inventors: Ning Luo, Fayetteville, AR (US); Trevor FOREIGN PATENT DOCUMENTS Newbold, Freeport (BS) CN 1837.180 A 9, 2006 CN 1837181 A 9, 2006 (73) Assignee: BioBases Technologies, LLC, GB 1248919 10, 1971 WO WO2004/099227 11, 2004 Springdale, AR (US) WO WO2005 123798 12/2005 WO WO2006/094227 A2 9, 2006 (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U.S.C. 154(b) by 461 days. Fornol et, al. in Fornol, A.R.; Onah, E., Ghosh, S.; Frazier, C.E.; Sohn, S.; Wilkes, G.L.; and Long, T.E., Synthesis and Characteriza (21) Appl. No.: 12/082,808 tion on Triglyceride-Based polyols and Tack-Free 15 Coatings Via The Air Oxidation of Soy Oil. J. Appl. Poly. Sci. (2006), 102:690 (22) Filed: Apr. 15, 2008 697.* Guo, A.; Javni, I; Petrovic, Z. Rigid Polyurethane Foams Based on (65) Prior Publication Data Soybean Oil. J. Appl. Poly. Sci. (2000), 77:467-473.* Zlatanic, A.; Lava, C.; Zhang, W.; Petrovic, Z. S. Effect of Structure US 2008/O262259 A1 Oct. 23, 2008 on Properties of Polyols and Polyurethanes Based on Different Veg etable Oils, 15 J. Poly. Sci.: Part B: Polymer Physics (2004), 42: Related U.S. Application Data 809-819. Guo, A.; Demydov, D.; Zhang, W.; Petrovic, Z. S. Polyols and (60) Provisional application No. 60/925,034, filed on Apr. Polyurethanes From Hydroformylation 5 of Soybean Oil, J. Polym. Environment (2002), iO (112): 49-52.* 18, 2007. Tran, P.; Graiver, D.; Narayan, R. Ozone-Mediated Polyol Synthesis From Soybean Oil. Journal of the American Oil Chemists Society 5 (51) Int. C. (2005), 82 (9), 653-719.* CD7C23/00 (2006.01) (52) U.S. Cl. ........................... 554/69;564/123: 568/852 (Continued) (58) Field of Classification Search .................... 554/69; Primary Examiner — Deborah D Carr 564/123: 568/852 (74) Attorney, Agent, or Firm — Stanley Baker See application file for complete search history. (57) ABSTRACT (56) References Cited A process for preparing natural oil hydroxylates, the process U.S. PATENT DOCUMENTS comprising reacting an amino compound containing 2002fOO58774 A1 5, 2002 Kurth et al. hydroxyl groups having a molecular weight of less than 200 2003. O191274 A1 10, 2003 Kurth et al. Daltons with vegetable oil derived polyols. 2004/0209971 A1 10, 2004 Kurth et al. 2006, O194974 A1 8/2006 Narayan et al. 23 Claims, 1 Drawing Sheet US 8,097,739 B2 Page 2 OTHER PUBLICATIONS Hu, Y.-H.; Gao, Y.; Wang, D.-N.; Hu, C.-P.; Zu, S.; Vanoverloop, L.; Randall, D. Rigid Polyurethane Foam 5 Prepared From a Rapeseed Petrovic, Z. S.; Zhang, W.; Jayni, I. Structure and Properties of Oil Based Polyol. Journal of Applied Polymer Science (2002), 84(3), Polyurethanes Prepared From Triglyceride Polyols by Ozonolysis, 591-597.* Biomacromolecules (2005), 6:713-719.* U.S. Appl. No. 10/924,332, filed Aug. 23, 2004, Casper, et al. Badrietal. In Production of a High-Functionality RBD Palm Kernel Oil-Based Polyester Polyol, Journal of Applied Polymer Science. Badri, K. H.; Ahmad, S.H.; Zakaria, S. (2001), 81(2), 384-389.* * cited by examiner U.S. Patent Jan. 17, 2012 US 8,097,739 B2 O y FG NR, O-> o O -N r1FG i. FG R Fig 2A OHis O - US 8,097,739 B2 1. 2 PROCESS FOR THE MANUFACTURE OF molecular weight measured with GPC using narrow molecu NATURAL OIL HYDROXYLATES lar weight distribution polystyrenes as standards. The exist ence of molecular weight distribution is inherent in the natu The present invention deals with a process for preparing ral oil origin. Polyols that are synthesized from this patent natural oilhydroxylates, said process comprising reacting an pending process are typically natural oil polyols and they are amino compound containing hydroxyl groups having a commercially available, under the brand name Agrol R, from molecular weight of less than 175 Daltons with vegetable oil BioBased Technologies, LLC, Rogers, Ark. derived polyols. This application claims priority from U.S. Monteavaro et al. in Monteavaro, L. L.; da Silva, E. O.; Provisional Patent Application Ser. No. 60/925,034, filed Apr. Costa, A. P. O.; Samios, D., Gerbase, A. E.; Petzhold, C. 18, 2007. 10 “Polyurethane Networks from Formiated Soy Polyols: Syn thesis and Mechanical Characterization. JAOCS (2005), 82: BACKGROUND OF THE INVENTION 365-371. (2005), prepared soy polyols with a one-step syn thesis using formic acid and hydrogen peroxide on the double Natural oil-derived polyols have been considered as alter bonds of the vegetable oils (3/1.5/1). natives for petroleum-based polyols for use in the polyure 15 This method followed the reaction steps of epoxidation of thane industry for making polyurethane materials. For mak unsaturated fatty acids followed by ring-opening of the epoxy ing polyurethane materials, proton-activated groups, such as groups to form polyols. By simply varying the reaction time hydroxyl groups, are necessary for the reactions with isocy at 65°C., the polyols that were formed had hydroxyl numbers anate groups that result in urethane linkages. Almost all of the that ranged from 53-162, acid numbers of 1.2-2.2 and vis commodity vegetable oils, except for castor oil, unfortu cosities in the range of 230-9844 cp. Molecular weights of the nately, contain no hydroxyl groups in their triacylglycerol polyols were reported up to 2404 Daltons. Based on the structures of Saturated and unsaturated fatty acids. However, description in this publication, the structure of the resultant the Supply of castor oil is restricted because of its growth in polyol is in the category of hydroxylated vegetable oil esters; limited geographical areas. however, the process forms a formic acid ester which is dif There is a need to chemically introduce hydroxyl groups 25 ferent than the acetic esters formed in the process of patent onto the triacylglycerols of the vegetable oils for the uses in application Ser. No. 10/924,332 A1 mentioned Supra. the polyurethane industry. U.S. patent application 2007/0123725 A1 describes a pro Polyurethanes are a class of polymeric materials with a cess for the preparation of polyols based on natural oils con wide spectrum of properties that make these materials of great Verting unmodified unsaturated fatty acid triglycerides into use to the daily life of mankind. For example, polyurethanes 30 polyols with peroxycarboxylic acids wherein phosphoric are used in furniture, clothing, automotive, carpets, and many acid is used as a catalyst and followed by an additional more applications in the form of foams, elastomers, coatings, alkoxylation step. In the step of preparing natural oil polyols adhesives, Sealants, and composites. and any further steps to modify the described natural oil In the U.S. patent application Ser. No. 10/924,332, filed on polyols, no amines or hydroxyalkylamines were used in this Aug. 23, 2004, Casper et al. claimed a simple, economic 35 patent application to form natural oil hydroxylates. process to produce polyols from vegetable oils. The process is Formolet. al. in Fornol, A. R.; Onah, E., Ghosh, S.; Frazier, a "one-pot' process using acetic acid and hydrogen peroxide C. E.; Sohn, S.; Wilkes, G. L.; and Long, T. E., Synthesis and to oxidize the double bonds of the unsaturated fatty acids of Characterization on Triglyceride-Based polyols and Tack the triacylglycerol structures thereby forming an epoxy Free Coatings Via The Air Oxidation of Soy Oil. J. Appl. Poly. group, and then conducting ring-opening of these epoxy 40 Sci. (2006), 102:690-697, applied dry-air oxidization on soy groups in situ with acetic acid at an elevated temperature. The bean oil to make polyols with hydroxyl numbers ranging from ring opening of an epoxy group with acetic acid generates a 7 to 110 mg KOH/g. Dry-air processes generated hydroxyl hydroxyl group and an adjacent acetate group simultaneously groups through the reactivity of adjacent protons of the at the C9, C12, or C15 sites of C18-C22 fatty acid carbon double bonds on the unsaturated fatty acids. This can lead to chains. Because the hydroxyl groups are generated near the 45 natural oil polyols produced without additional ester forma middle of the fatty acid chains, such hydroxyl groups are tion. secondary hydroxyl groups. U.S. Patent publication 2002/0058774 in the name of Tho No additional catalyst was needed in this process. No inor mas Kurth, et al describes a method to produce vegetable oil ganic acids were used in this process as well. The final polyols polyols in a transesterification process from a vegetable oil produced from this process are composed of triacyl-glycerol 50 polyol with a multifunctional alcohol to form a polyol with structures as the basic units but somehow a portion of them selectable functionality. can be linked together so that these dimer or higher oligomer WO Publication 2006/094227A2 and U.S. Patent publica ized triacylglycerol units result in giving an average molecu tion 2007/0173632 describes a method using an iron-contain lar weight of the polyols that is about twice as high as that ing catalyst in an oxidation process to produce natural oil compared with the unhydroxylated initial triacylglycerols. 55 derived polyols having an increased hydroxyl number in In the triacylglycerol units of the polyols produced from which the hydroxyl number was as high as 220 mg KOH/g.
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