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United States Patent (19) 11 Patent Number: 5,646,098 Brois 45 Date of Patent: Jul

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United States Patent (19) 11 Patent Number: 5,646,098 Brois 45 Date of Patent: Jul US005646098A United States Patent (19) 11 Patent Number: 5,646,098 Brois 45 Date of Patent: Jul. 8, 1997 (54) CARBONYL CONTAINING COMPOUNDS 4,025,445 5/1977 Hellmuth et al. ...................... 252/49.6 AND THER DERVATIVES AS MULT. 4,328,113 5/1982 Horodysky et al. ................... 252A49.6 FUNCTIONAL FUEL AND LUBE ADDITIVES 4,329,239 5/1982 Chou ............... ... 252/51.5A 4,474,670 10/1984 Braid et al. .. ... 252A327 E 4,474,671 10/1984 Herd et al. ............................. 252A33.6 (75) Inventor: Stanley J. Brois, Westfield, N.J. 4,524,004 6/1985 Horodysky ...... ... 252A327 E 4,524.005 6/1985 Horodysky ............................. 252A9.6 (73) Assignee: Exxon Chemical Patents Inc, Linden, 4,529,529 7/1985 Horodysky ...... ... 252A9.6 N.J. 4,566,984 1/1986 Bush ....................................... 252/140 4,599,183 7/1986 Horodysky et al. ... 252A327 E 21 Appl. No.: 242,750 4,925,983 5/1990 Stockel ....................................... 56.4/8 4,961,868 10/1990 Doner et al. 252/32.7 E 22) Fied: May 13, 1994 5,057,564 10/1991 Brois ....................................... 524/101 5,084,194 1/1992 Doner et al. ... 252/327 E Related U.S. Application Data 5,211,860 5/1993 Doner et al. ....................... 252/327 E 5,274,051 12/1993 Brois et al. ............................. 525/383 63 Continuation-in-part of Ser. No. 48,625, Apr. 16, 1993, 5,277,833 1/1994 Song et al... ... 252/56 R abandoned, which is a continuation-in-part of Ser. No. 5,288,811 2/1994 Brois ....................................... 525/383 927,990, Aug. 11, 1992, abandoned, which is a continuation of Ser. No. 844,064, Mar. 2, 1992, abandoned, which is a FOREIGN PATENT DOCUMENTS continuation-in-part of Ser. No. 775,878, Oct. 11, 1991, abandoned, which is a continuation-in-part of Ser. No. 650770 11/1964 Belgium ...................... COM 33/58 556,243, Jud. 23, 1990, Pat. No. 5,057,564. 099478A3 2/1984 European Pat. Off. ........ C08C 19/00 105772 4/1984 European Pat. Off. ... CO7C 49/245 (51) Int. Cl. ............. C10M 159/12; C10M 129/86; 0132383A2 1/1985 European Pat. Off. ... C10M 133/52 C10M 139/00 264247 4/1988 European Pat. Off. ..... C1OM 129/95 52 U.S. Cl. ................ 508/189; 508/190; 508/198; 2344.625 3/1977 France .............................. C10 1/8 508/221; 508/222; 508/452; 508/575; 525/374; WO91/16408 10/1991 WIPO ............................... COL 1/22 525/375; 525/383; 525/385; 526/213; 526/269; WO95/15303 6/1995 WIPO ............................ CO7C 59/21 528/222; 544/221; 54.6/13; 54.6/155: 548/110; OTHER PUBLICATIONS 548/544; 549/4; 549/285; 549/292; 549/295; 560/170; 560/174; 560/190; 562/567; 562/578; Chemical Abstracts, vol. 81, No. 18, Nov. 4, 1974, Colum 562/590; 564/160; 568/1; 568/3: 568/376; bus, Ohio, U.S. Abstract No. 108403y, Zalukaev et al. 568/379 “Lubricating Composition” p. 175, col. 2. 58) Field of Search ...................... 546/13, 155; 548/110, Primary Examiner Jerry D. Johnson 548/544; 549/4, 285,292, 295; 568/1, 3, Attorney, Agent, or Firm-Harvey L. Cohen 376,379; 525/383,375,374,385, 386; 526/213, 269; 528/222; 544/221; 560/170, 57 ABSTRACT 174, 190; 562/567,578, 590: 564/160; The invention relates to novel compositions comprising ene 252/32, 49.6, 51.5 R, 52 R, 56 R; 508/189, and free radical adducts of unsaturated and saturated 190, 198, 221, 222, 452, 575 hydrocarbons, and acyclic and cyclic vicinal polycarbonyl compounds such as diethyl ketomalonate and indantrione. 56 References Cited The adducts are reacted with nucleophiles such as amines, U.S. PATENT DOCUMENTS electrophiles such as anhydrides and esters, and metal ions. 3,087,936 4/1963 Le Suer ............................... 260/326.3 Post-products are obtained via reaction of said products with 3,115,398 12/1963 Thayer ........................................ 44/66 capping reagents such as boric acid. Compositions contain 3,322,670 5/1967 Burt et al. 252/49.6 ing said adducts, products and post-products include oleagi 3,328,463 6/1967 Lee et al. ................................ 260/566 nous substances such as fuels and lube oils. 3,344,069 9/1967 Stuebe .................................... 252A49.6 4,011,167 3/1977 Chibnik et al. ........................ 252/42.7 11 Claims, No Drawings 5,646,098 1. 2 CARBONYL CONTANNG COMPOUNDS novel compounds derived from said ene and radical adducts, AND THER DERVATIVES AS MULT. and are referred to herein as "products,” and novel com FUNCTIONAL FUEL AND LUBE ADDITIVES pounds derived from said products, and referred to herein as RELATED APPLICATIONS "post-products,” their method of preparation, and composi The application is a continuation in part of U.S. Ser. No. 5 tions containing the same. Thus, non-limiting embodiments 048,625, filed Apr. 16, 1993 and now abandoned; which is of the invention include: (a) oleaginous compositions con a continuation-in-part of U.S. Ser. No. 927.990, filed Aug. taining a major amount of an oleaginous substance and a 11, 1992, abandoned; which is a Rule 60 continuation of minor amount of an ene or radical adduct of at least one VP U.S. Ser. No. 844,064, filed Mar. 2, 1992, abandoned; which monomer and a hydrocarbon having a number average is a continuation-in-part of U.S. Ser. No. 775,878, filed Oct. 10 molecular weight (M) in the range of about 200 to about 10 11, 1992, abandoned; which is a continuation-in-part of U.S. million; (b) oleaginous compositions comprising a major Ser. No. 556.243, filed Jul. 23, 1990, U.S. Pat. No. 5,057, amount of an oleaginous substance and a minor amount of 564. a productformed by reacting: (i) a compound selected from the group consisting of ene and radical adducts, with (ii) a FIELD OF THE INVENTION 15 compound selected from the group consisting of amines, This invention relates to novel carbonyl containing com polyamines, amino alcohols, alcohols, polyols, hydrazines, pounds and their derivatives as additives useful in oleagi derivatives of hydrazines, hydroxylamines, semicarbazides, nous compositions such as fuels, lubricants, power trans hydrides, cyanohydrins, phosphites, carbon acids and metal mission fluids, and the like. ions; and (c) oleagineous compositions comprising a major 20 amount of an oleaginous substance and a minor amount of BACKGROUND OF THE INVENTION a post-product formed by reacting: (i) a compound selected Oleaginous substances have found wide use in contem from the group consisting of ene and radical adducts, with porary industry. Unfortunately, many oleaginous composi (ii) a compound selected from the group consisting of tions contain additives that from an environmental view amines, polyamines, amino alcohols, alcohols, polyols, point could be improved. For example, many additives used 25 hydrazines, derivatives of hydrazines, hydroxylamines, today contain chlorine which is environmentally undesir semicarbazides, hydrides, cyanohydrins, phosphites, and able. Therefore, there is a need for chlorine-free additives. carbon acids to form a product; and then reacting said Also, many of today's high performance applications for product with (iii)borating, acylating, and thio acid reagents, oleaginous compositions require additives that can meet as well as metal ions to form a post-product. multi-functional requirements. Therefore, any environmen 30 In a special embodiment of the present invention, tally acceptable additives for oleaginous compositions chlorine-free dispersants are provided comprising adducts of should preferably provide the benefits of multi-functional VP monomers and polyisobutylenes, ethylene alpha-olefin properties. copolymers, ethylene butene copolymers, poly-alpha One approach to providing such additives for oleaginous olefins, and poly-n-butenes having M values ranging from compositions is to take advantage of the unique multi 35 functional properties of the novel carbonyl compounds about 500 to about 20,000 (20K) that have been aminated described hereinafter by preparing oleaginous compositions with polyamines, such as tetraethylene pentamine. containing the chlorine-free adducts and derivatives of this These and other embodiments will be set forth in greater invention. detail in the general description which follows. Organic compounds containing two or more carbonyl General Description groups in a row are generally referred to as vicinal polycar In its broadest sense, the present invention is concerned bonyl (VP) monomers. When the vicinal polycarbonyl (VP) with a new family of compounds consisting of (a) ene and group forms part of an acyclic hydrocarbon structure, such radical adducts having one or more VP monomers per compounds are generally referred to as acyclic VP mono adduct, (b) products derived from said ene and radical mers. When the polycarbonyl group forms part of a cyclic 45 adducts, and (c) post-products derived from said products, structure, such compounds are generally referred to as cyclic which are useful in oleaginous compositions, especially as VP monomers. multifunctional additives, dispersants, and dispersant vis The reactions of VP monomers with unsaturated cosity modifiers. The adducts are prepared via the ene and hydrocarbons, including unsaturated hydrocarbon polymers, radical addition of VP monomers to unsaturated and satu will produce carbonyl containing adducts as disclosed in 50 rated hydrocarbons and polymers respectively, with M. U.S. Pat. No. 5,057,564 and Application Ser. No. 935,604. values ranging from about 200 to about 10 million. These adducts are referred to herein as ene adducts. Moreover, the hydrocarbon and polymer reactants may More recently, various hydrocarbons, and especially satu contain one or more polar substituents, provided that the rated hydrocarbons, and saturated hydrocarbon polymers, polar substituents are compatible with the ene and radical have been found to react with VP monomers in the presence 55 chemistry involved in the functionalization with VP mono of a free radical initiator.
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