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WO 2012/129477 Al 27 September 2012 (27.09.2012) P O P C T

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WO 2012/129477 Al 27 September 2012 (27.09.2012) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2012/129477 Al 27 September 2012 (27.09.2012) P O P C T (51) International Patent Classification: HATEGAN, Georgeta [US/US]; 1859 Goss C , Plain- CIOM 129/72 (2006.0 1) C08F 20/68 (2006.01) field, Illinois 60586 (US). CIOM 133/16 (2006.01) C08F 210/14 (2006.01) (74) Agent: DUCHEZ, Neil, A.; Renner, Otto, Boisselle & Sk- CIOM 159/20 (2006.0 1) CI ON 10/02 (2006.01) lar, LLP, 1621 Euclid Avenue, 19th Floor, Cleveland, Ohio CIOL 1/18 (2006.01) CION 10/04 (2006.01) 441 15-2191 (US). CIOL 1/22 (2006.01) CION 10/06 (2006.01) CllC 3/00 (2006.01) CION 10/08 (2006.01) (81) Designated States (unless otherwise indicated, for every C08F 20/14 (2006.01) CION 10/10 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/US20 12/030282 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (22) International Filing Date: HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, 23 March 2012 (23.03.2012) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (25) Filing Language: English OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/467,273 24 March 201 1 (24.03.201 1) US (84) Designated States (unless otherwise indicated, for every 61/467,275 24 March 201 1 (24.03.201 1) US kind of regional protection available): ARIPO (BW, GH, 61/467,276 24 March 201 1 (24.03.201 1) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 61/467,279 24 March 201 1 (24.03.201 1) US UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, 61/467,292 24 March 201 1 (24.03.201 1) US TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, 61/5 10,159 2 1 July 201 1 (21.07.201 1) US DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, 13/281,108 25 October 201 1 (25. 10.201 1) US LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (71) Applicant (for all designated States except US): ELEV- GW, ML, MR, NE, SN, TD, TG). ANCE RENEWABLE SCIENCES [US/US]; 2501 Dav- ey Road, Woodridge, Illinois 605 17 (US). Published: (72) Inventors; and — with international search report (Art. 21(3)) (75) Inventors/Applicants (for US only): DIBIASE, Stephen — before the expiration of the time limit for amending the Augustine [US/US]; 405 61st Street, Willowbrook, Illinois claims and to be republished in the event of receipt of 60527 (US). RIZVI, Syed, Q.A. [US/US]; 1765 North amendments (Rule 48.2(h)) Ashwood Lane, Painesville, Ohio 44077 (US). - (54) Title: FUNCTIONALIZED MONOMERS (57) Abstract: This invention relates to functionalized monomers which are reacted with an enophilic reagent (e.g., maleic anhyd - ride) to form an enophilic reagent modified functionalized monomer. The enophilic reagent modified functionalized monomer may be further reacted with one or more additional reagents (e.g., oxygen-containing reagents, nitrogen-containing reagents, metals or metal compounds). The invention relates to base oils which may comprise functional base oils. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and functional compositions (e.g., cleaning solutions, food products, etc.). Title: FUNCTIONALIZED MONOMERS This application is a continuation-in-part under 35 U.S.C. § 120 of U.S. Application Serial No. 13/281 ,108, filed October 25, 201 1. A claim of priority for this application under 35 U.S.C. § 1 19(e) is hereby made to the following U.S. provisional patent applications: U.S. Serial No. 61/51 0,1 59 filed July 2 1, 201 1; U.S. Serial No. 61/467,273 filed March 24, 201 1; U.S. Serial No. 61/467,275 filed March 24, 201 1; U.S.Serial No. 61/467,276 filed March 24, 201 1; U.S. Serial No. 61/467,279 filed March 24, 201 1; and U.S.Serial No. 61/467,292 filed March 24, 201 1. These applications are incorporated herein by reference. Technical Field This invention relates to functionalized monomers, and to lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, dispersants, detergents, polymeric resins or plastics, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemicals, agriculatural chemicals, and the like. Background Monomers are often mono-functional in nature. This limits potential uses for derivatives. Summary The functionalized monomers of the present invention may be difunctional or polyfunctional. These monomers offer flexibility as well as means to prepare novel derivatives with utility in a wide breadth of applications. These monomers may undergo high degrees of polymerization, resulting in polymers of unique molecular weight distributions and structural shapes, some of which may have use as specialty polymers to be employed in new applications. The term "polymer" is used herein to refer to polymers, including homopolymers and copolymers, as well as oligomers and co-oligomers. The functionalized monomers of the present invention may be derivatized to provide compounds with unique properties that are easy to process and are bio-compatible. The functionalized monomers as well as the derivatives derived from such functionalized monomers may have utility in many applications and products, such as lubricants, functional fluids, fuels, dispersants, detergents, molded or extruded articles, pharmaceuticals, cosmetics, personal care products, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemicals, agricultural chemicals, and the like. The functionalized monomers and/or derivatives may be used as base oils for lubricants and functional fluids, and for providing functional additives for lubricants, functional fluids and fuels. When used as base oils, these functionalized monomers and/or derivatives may be referred to as functional base oils. These functional base oils may be used in the lubricants and functional fluids as base oils, and may also provide additional properties to the lubricant or functional fluid, such as dispersency, and the like, that in the past would have been provided by supplemental additives. The present invention may provide for an advantageous balance between various performance characteristics while selecting suitable monomers and derivatives that are compatible with acceptable manufacturing techniques. The functionalized monomer may be derived from natural products, for example, natural oil, metathesized natural oil, carbohydrates, and the like. The functionalized monomer may be derived from one or more estolides. The natural oils, metathesized natural oils, carbohydrates and estolides employed herein may provide the advantage of comprising or being derived from renewable sources (e.g., vegetable oils, animal fats or oils, and the like) and may be obtained using environmentally friendly production techniques with less energy than conventional processes for making lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, including dispersants and detergents, polymeric resins, adhesives, coatings, pharmaceuticals, cosmetics, personal care products, industrial cleaners, institutional cleaners, foods, beverages, oil field chemicals, agricultural chemicals, and the like, derived from petroleum. This technology may be referred to as "green" technology. Synthetic lubricants are commonly used in passenger car motor oils, heavy-duty diesel engine oils, marine and railroad engine lubricants, automatic transmission fluids, hydraulic fluids, gear oils, and industrial lubricants, such as metalworking fluids and lubricating greases. The purpose of these oils is to provide improved friction and wear control, rapid dissipation of heat, and the dissolution of and/or facilitating the removal of service-related contaminants. Achieving a proper balance between various performance characteristics is an important consideration in selecting a synthetic lubricant for a particular application. For example, polyolefin based lubricants typically exhibit good low- temperature properties, high viscosity index, and excellent thermal stability, but poor solvency. As a result, these lubricants tend to be inadequate without the presence of additional polar base stock-containing components. Conversely, polar base stock-containing lubricants, such as those based on synthetic esters and vegetable oils, typically exhibit good solvency and high surface affinity. However, these lubricants tend to be inadequate with respect to resistance to wear. The problem, therefore, is to provide a synthetic lubricant that exhibits both good solvency and good resistance to wear reduction characteristics. This invention provides a solution to this problem. Ashless dispersants are additives used in lubricants, functional fluids and fuels to prevent oxidation-derived deposits from impairing function. Lubricants, functional fluids and fuels that employ these additives include passenger car motor oils, heavy-duty diesel engine oils, marine and railroad engine lubricants, automatic transmission fluids, gear oils, and the like, with the largest use typically being in automotive and industrial engine oils. The amount of dispersant used in a lubricant or functional fluid depends upon the specific application but, typically, constitutes from about 0.1 percent to about 30 percent by weight of the lubricant or functional fluid. In fuels, the amount of dispersant is typically less than in lubricants or functional fluids.
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