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(12) Patent Application Publication (10) Pub. No.: US 2010/0217022 A1 Abraham Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0217022 A1 Abraham Et Al US 2010O2.17022A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0217022 A1 Abraham et al. (43) Pub. Date: Aug. 26, 2010 (54) ENHANCED OLGOMERIC POLYOLS AND Related U.S. Application Data POLYMERS MADE THEREFROM (60) Provisional application No. 60/795.327, filed on Apr. 27, 2006, provisional application No. 60/859,337, (76) Inventors: Timothy W. Abraham, filed on Nov. 16, 2006. Minnetonka, MN (US); Jeff Malsam, Minneapolis, MN (US); Publication Classification Xiuguang A. Guo, Pittsburg, KS (51) Int. Cl. (US); Milhail Ionescu, Pittsburg, CIIC 3/00 (2006.01) KS (US); Ivan J. Javni, Pittsburg, (52) U.S. Cl. ........................................................ 554/163 KS (US); Zoran S. Petrovic, Pittsburg, KS (US) (57) ABSTRACT Enhanced oligomeric polyols are reported. The enhanced Correspondence Address: oligomeric polyols may be prepared by a method comprising CARGILL, INCORPORATED the steps of: (a) providing an oligomeric polyol that com P.O. Box 5624 prises at least one glycerol fatty acid ester having at least one MINNEAPOLIS, MN 55440-5624 (US) glycerol fatty acid ester bond; wherein at least 5% of the ethyldenyl groups (*C—C) in the glycerol fatty acid ester (21) Appl. No.: 12/226,696 are substituted with a bonding structure selected from the group consisting of C C C*—C: O C C*—O; (22) PCT Fled: Apr. 27, 2007 —*C C*—C, and mixtures thereof, where * is used to denote the original carbonatoms in the ethylidenyl group; and (86) PCT NO.: PCT/US07/10252 (b) cleaving at least a portion of the glycerol fatty acid ester bonds to form the enhanced oligomeric polyol. The enhanced S371 (c)(1), oligomeric polyols are useful in making polymers such as (2), (4) Date: May 7, 2010 polyurethanes. US 2010/0217022 A1 Aug. 26, 2010 ENHANCED OLGOMERIC POLYOLS AND rapeseed oil, tung oil, peanut oil, castor oil, jatropha oil, and POLYMERS MADE THEREFROM combinations thereof. Examples of animal fats include fish oil, lard, and tallow. CROSS-REFERENCE TO RELATED 0009. In exemplary embodiments, the oligomerization of APPLICATIONS the natural oil may be accomplished by chemical oligomer ization (e.g., epoxidation and ring opening oligomerization) 0001. This application claims priority to U.S. Ser. No. or by anaerobic thermal oligomerization (e.g., anaerobic 60/795.327 entitled “Enhanced Oligomeric Polyols', filed heating to form a bodied oil). After oligomerization, at least a Apr. 27, 2006, and to U.S. Ser. No. 60/859,337, entitled portion of the glycerol fatty acid ester bonds in the oligomeric “Viscoelastic Polyurethane Foams Comprising Amidated or natural oil are cleaved to form an enhanced polyol of the Transesterified Oligomeric Natural Oil Polyols', filed Nov. invention. Cleaving at least a portion of the glycerol fatty acid 16, 2006, the disclosures of which are incorporated herein by ester bonds functions to introduce additional functionality reference. (i.e., to "enhance' the functionality of the oligomeric fatty acid ester) into the oligomeric fatty acid ester. For example, in BACKGROUND many embodiments, the cleaving reaction introduces primary 0002 Petroleum-derived polyols have been widely used in hydroxyl functionality into the enhanced oligomeric polyols. the manufacturing of polyurethane foams. Recently, how 0010 Representative examples of cleaving reactions ever, there has been an increased interest in the use of renew include reacting the oligomeric natural oil with a nucleophile. able resources in the manufacturing of polymers such as Common nucleophilic cleaving reactions include amidation polyurethanes. This has led to research into developing natu and transesterification. ral oil-based polyols that are suitable as full or as partial 0011 Amidation involves reacting the oligomeric natural replacements for petroleum-derived polyols in polymers such oil with an amine (e.g., a polyamine Such as a diamine) or an as polyurethanes. alkanolamine (eg. ethanolamine). During amidation, at least 0003. One method of making a polyol from an unsaturated a portion of the amine groups that are present in the natural oil is to epoxidize the natural oil, followed by ring polyamine react with at least a portion of the ester groups that opening of at least a portion of the epoxide groups to form are present in the oligomeric natural oil resulting in the for pendant secondary hydroxyl groups. Ring-opening may be mation of amide groups and hydroxyl groups. accomplished, for example, by reacting the epoxidized natu 0012 Transesterification involves reacting the oligomeric ral oil with a alcohol (e.g., methanol) in the presence of a natural oil with a polyol (e.g., diol) compound. During trans catalyst (e.g., HBF4). This synthetic route results primarily in esterification, at least a portion of the ester groups that are the formation of secondary hydroxyl groups that are pendant present in the polyol compound react with at least a portion of from the natural oil. Although pendant secondary hydroxyl the ester groups that are present in the oligomeric natural oil groups are useful in forming polyurethanes, it is desirable to resulting in the formation of ester groups and hydroxyl provide natural oil-based polyols that have faster reactivity groups. due to the presence of at least Some primary hydroxyl groups 0013 Throughout the application, the following terms in the polyol. will have the following meanings. 0014. As used herein “polyol refers to a molecule that has an average of greater than 1.0 hydroxyl groups per molecule. SUMMARY It may optionally include other functionalities. 0004. The present invention relates to enhanced oligo 0015. As used herein “anaerobic thermal oligomeriza meric polyols that are prepared from natural oils. The natural tion” refers to the process of oligomerizing a fatty acid ester oil polyols may be used to make polymers such as polyure (e.g., natural oil) by the application of heat under Substan thanes, polyesters, polycarbonates, and the like. In exemplary tially anaerobic conditions. embodiments, the natural oil polyol are useful in polyure 0016. As used herein “chemical oligomerization” refers to thane polymers, such as polyurethane foams. the process of oligomerizing a fatty acid ester (e.g., natural 0005. In some embodiments of the invention, the oil) by a chemical process that includes creating cross-links enhanced oligomeric polyols are prepared by a method com between fatty acid chains by functionalizing (e.g., epoxidiz prising the steps of ing) at least a portion of the double bonds in the fatty acid ester 0006 (a) providing an oligomeric polyol that comprises and reacting (e.g., ring-opening) at least a portion of the at least one glycerol fatty acid ester having at least one functional groups to create cross-links. glycerol fatty acid ester bond; wherein at least 5% of the 0017. As used herein “natural oil means a plant-based oil ethylidenyl groups (*C—C) in the glycerol fatty acid (i.e., a vegetable oil) or an animal fat. ester are substituted with a bonding structure selected 0018. As used herein “oligomer refers to two or more from the group consisting of C C C C: glyceride-based fatty acid ester monomerunits that have been O *C C* O; C–*C C*- C, and mixtures covalently bonded to one another by an oligomerizing reac thereof, where * is used to denote the original carbon tion. Oligomers include dimers, trimers, tetramers, and atoms in the ethylidenyl group; and higher order oligomers. The term "oligomerized’ refers to a 0007 (b) cleaving at least a portion of the glycerol fatty material that comprises oligomers. acid ester bonds to form the enhanced oligomeric polyol. DETAILED DESCRIPTION 0008 Examples of natural oils that may be useful as start ing materials include plant-based oils (e.g., vegetable oils) 0019. The invention relates to polyols that are derived and animal fats. Examples of plant-based oils include Soy from natural oils, such as Vegetable oils or animal fats. bean oil, safflower oil, linseed oil, corn oil, Sunflower oil, 0020. In order to make the enhanced oligomeric polyol, a olive oil, canola oil, Sesame oil, cottonseed oil, palm oil, starting composition comprising a natural oil is oligomerized US 2010/0217022 A1 Aug. 26, 2010 by an oligomerization method Such as chemical oligomeriza For example, a vegetable oil having one double bond per tion oranaerobic thermal oligomerization. After oligomeriza molecule corresponds to an iodine value of about 28. Soybean tion, at least a portion of the glycerol fatty acid ester bonds in oil typically has about 4.6 double bonds/molecule and has an the oligomerized fatty acid ester are cleaved in order to intro iodine value of about 120 to about 140. Canola oil typically duce additional functionality into the polyol. Cleaving the has about 4.1 double bonds/molecule and has an iodine value fatty acid ester bonds may be accomplished, for example, by of about 115. Typically, iodine values for the vegetable oils reaction with a nucleophile. Common nucleophilic reactions will range from about 40 to about 240. In some embodiments, include amidation and transesterification. Representative Vegetable oils having an iodine value greater than about 80, examples of enhanced oligomeric polyols include: (a) ami greater than about 100, or greater than about 110 are used. In dated anaerobically thermally oligomerized polyols; (b) ami Some embodiments, vegetable oils having an iodine value less dated chemically oligomerized polyols; (c) transesterified than about 240, less than about 200, or less than about 180 are anaerobically thermally oligomerized polyols; and (d) trans used. esterified chemically oligomerized polyols. 0029. Useful natural oils typically comprise glycerides 0021. In some embodiments, the enhanced oligomeric (e.g., mono, di, and triglycerides) of fatty acids that contain polyols are prepared by amidating an anaerobically thermally glycerol fatty acid ester bonds, which link the fatty acids to oligomerized natural oil. Such polyols may be made by a the glycerol molecule in the glyceride.
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