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United States Patent [191 [11] Patent Number: 4,478,732 Horodysky Et Al

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United States Patent [191 [11] Patent Number: 4,478,732 Horodysky Et Al United States Patent [191 [11] Patent Number: 4,478,732 Horodysky et al. [45] Date of Patent: a. Oct. 23, 1984 [54] FRICTION REDUCING ADDITIVES AND [56] References Cited COMPOSITIONS THEREOF U.S. PATENT DOCUMENTS [75] Inventors: Andrew G. Horodysky, Cherry Hill; 3,117,089 1/1964 De Young et a1. .......... .. 252/321 E Joan M. Kaminski, Clementon, both 3,235,498 2/1966 Waldmann ........... .. of NJ. 4,298,486 11/1981 Horodysky m1. ............. .. 252/49.6 [73] Assignee: Mobil Oil Corporation, New York, Primary Examiner-—Jacqueline V. Howard NY. Attorney, Agent, or Firm—Alexander J. McKillop; [*1 Notice: - The portion of the term of this patent Michael G. Gilman; Howard M. Flournoy subsequent to Nov. 3, 1998 has been [57] ABSTRACT disclaimed. Certain borated additive compounds, such as borated [21] Appl. No.: 265,301 mixed ethoxylated amines and ethoxylated amides or hydroxyalkyl imidazolines and hydroxyesters or hydro [22] Filed: May 20, 1981 lyzed hydroxyalkyl imidazolines and ethoxylated am [51] Int. Cl.3 ....................... .. C10M 1/54; ClOM 1/10 ides and combinations thereof, provide highly effective [52] US. Cl. ................................. .. 252/49.6; 548/110; ‘multifunctional characteristics for various lubricating 548/347; 252/51.5 R media into which they are incorporated. [58] Field of Search ....................... .. 252/49.6, 51.5 R; 548/347, 110 10 Claims, No Drawings 4,478,732 ll 2 example, reduced friction and increased oxidative and FRICTION REDUCING ADDITIVES AND thermal stability and to a method of reducing fuel con COMPOSITIONS THEREOF sumption in internal combustion engines by treating the moving surfaces thereof with said compositions. BACKGROUND OF THE INVENTION DESCRIPTION OF SPECIFIC EMBODIMENTS 1. Field of the Invention This invention relates to lubricant additives and com The generalized structure of the hydroxyalkyl or positions thereof and, more particularly, to lubricant hydroxyalkenyl hydrocarbyl amides useful herein be compositions having multifunctional capabilities com fore boration, is: ‘ prising oils of lubricating viscosity or greases prepared therefrom containing a minor amount of said multifunc o (cum-120),}: tional additive which is derived from various borated ll / mixtures of hydroxyesters, ethoxylated hydrocarbyl R-CN amines, ethoxylated hydrocarbyl amides, hydroxyalkyl (cnzcnzmyn or hydroxyalkenyl hydrocarbyl imidazolines, or hydro 15 lyzed hydroxyalkyl or hydroxyalkenyl hydrocarbyl where R usually will contain from about 10 to 30 car imidazolines. bon atoms and is an alkyl or substituted alkyl group 2. Description of the Prior Art which may be primary, secondary or tertiary, straight Currently there is a serious effort on the part of the 20 chain, branched, or cyclic and may contain one or more automotive industry and the oil industry to provide double bonds, halogen or one or more sulfur atoms or means for prolonging engine life and reducing the an aromatic ring. x and y may be the same or different amount of fuel consumed by internal combustion en and each is from 1 to about 10, however, the sum of x gines. Many solutions have been tried; some strictly and y must always be 2 or greater. Propoxylated amides mechanical, some have been done with lubricating oils 25 can also'be used. A few examples of the above described and some have been done by adding friction reducing amide structure include bis(2-hydroxyethyl) oleamide, additives thereto. It has now been found that certain borated mixed hydroxy esters and hydrolyzed hydroxy bis(Z-hydroxyethyl) cocoamide, bis(2-hydroxyethyl) alkyl or hydroxyalkenyl hydrocarbyl imidazolines; bo soyamide, bis(2-hydroxyethyl) octadecylamide, poly rated mixed hydrolyzed hydroxyalkyl or hydroxyalke oxyethylene (5) oleamide, polyoxyethylene (4) cocoa nyl hydrocarbyl imidazolines and hydroxyalkyl or hy 30 mide, polyoxyethylene (5) soyamide, etc. droxyalkenyl hydrocarbyl imidazolines; borated mixed The generalized structure of the hydroxyalkyl or ethoxylated hydrocarbyl amides and hydrolyzed hy hydroxyalkenyl hydrocarbyl amines, in accordance droxyalkyl or hydroxyalkenyl hydrocarbyl imidazo herewith before boration, is: lines; borated mixed ethoxylated hydrocarbyl amines and hydrolyzed hydroxyalkyl or hydroxyalkenyl hy 35 drocarbyl imidazolines; borated mixed ethoxylated hy drocarbyl amines and hydroxyesters; borated mixed ' ethoxylated hydrocarbyl amides and hydroxyesters; borated mixed hydroxyalkyl or hydroxyalkenyl hydro carbyl imidazoline and hydroxyesters; borated mixed 40 and as stated hereinabove x and y may be the same or ethoxylated hydrocarbyl amines and ethoxylated hy different and each is from 1 to about 10, with the pro drocarbyl amides; borated mixed ethoxylated hydro viso that the sum of x and y must be 2 or greater. A carbyl amides and hydroxyalkyl or hydroxyalkenyl non-exhaustive list of examples include bis(Z-hydrox hydrocarbyl'imidazolines; borated mixed ethoxylated yethyl) oleylamine, bis(2-hydroxyethyl) soyamine, hydrocarbyl amines and hydroxyalkyl or hydroxyalke 45 bis(Z-hydroxyethyl) cocoamine, bis(2-hydroxyethyl) nyl hydrocarbyl imidazolines, and borated mixtures of octadecylamine, polyoxyethylene (5) oleylamine, poly various such combinations provide multifunctional oxyethylene (5) soyaamine, polyoxyethylene (4) cocoa characteristics that are not obtainable with the individ mine, etc. ual borated materials or physical mixtures of such bo The generalized structure of the hydroxyesters, use rated materials. The borated derivatives disclosed 50 ful herein before boration, is exemplified by the follow herein provide improved oxidative and thermal stabil mg: ity, volatility, bearing corrosion inhibiting properties and friction reduction relative to the individual borated materials. These borated mixtures are to the best of applicants’ knowledge novel and unknown heretofore 55 and thus accordingly have not been previously used in the lubricating art. SUMMARY OF THE INVENTION This invention is directed to novel, additive com 60 where R'=CH2OH, CH3 or H pounds, that is, borates of mixed hydroxy esters, ethox R”=CH2OH, H, or CRZ'OCOR ylated hydrocarbyl amines, ethoxylated hydrocarbyl y=l to 5 amides, hydroxyl alkyl or hydroxyalkenyl hydrocarbyl The hydroxy esters must contain at least one free imidazolines, and hydrolyzed hydroxyalkyl or hydrox hydroxyl group but may contain two or more. The yalkenyl hydrocarbyl imidazolines in various combina 65 hydroxy esters may also contain one ester group (as is tions. In addition to these novel compounds, the inven glycerol monooleate) or more (as is glycerol dioleate). tion is also directed to lubricant compositions having The esters can be used in pure form, or preferably in significant multifunctional characteristics, such as for mixtures such as mixtures of glycerol mono- and diole 4,478,732 3 4 ate. R is a hydrocarbyl group having from about 10 to their multifunctional characteristics even after being in about 30 carbon atoms and said hydrocarbyl moiety the presence of water at elevated temperatures. may be alkyl, straight or branched, cyclic or substi Exemplary mixed borates so prepared are mixed hy tuted; and may contain one or more double bonds, halo droxyalkyl or hydroxyalkenyl hydrocarbyl imidazo gen or one or more sulfur atoms or aromatic rings and line-ethoxylated hydrocarbyl amine borates such as: y is 1 to about 5. The hydroxy esters may be made by the reaction of polyhydroxy alcohols with organic acids where glycerol and oleic acid are used in the prepara tion of glycerol monooleate. Thioglycerol hydroxyes ters can also be used. Sorbitan hydroxyesters and hydroxyesters prepared from trimethylolpropane and pentaerythritol are also useful, e.g., sorbitan monooleate, trimethylolpropane The mixed hydrolyzed hydroxyalkyl or hydroxyalke monooleate, trimethylolpropane dioleate, pentaerythri nyl hydrocarbyl imidazoline-ethoxylated hydrocarbyl tol dioleate monolaurate and the like. amide borates included in the present invention are such Also useful are hydroxylalkyl or hydroxyalkenyl alkyl or alkenylimidazolines and/or hydrolysis prod as ucts of the imidazoline. The general structure of such compounds can be as described below: CHZCHZ (OCH CH) O 20 / 2 2\ n 25 R is de?ned above. A generalized structure of useful mixed ethoxylated hydrocarbyl amine-ethoxylated hydrocarbyl amide bo where R is about 10-30 carbon atoms and may be alkyl rates is as follows: or alkenyl, arylalkyl, alkyl aryl etc. and x is 1 to 5. Their respective ring-opened hydrolysis products are made 0 (cnzcuzon by treatment of the above-described imidazolines with / at least molar amounts of water and result in structures \ such as: (CH2CH20)y / 35 (HOCHgCI-l2)y Various similar or related ring-opened borate struc tures, where R, x, and y are as previously de?ned above, are also included with all of the mixed borates 40 disclosed hereinabove. Mixed hydroxyester-ethoxylated hydrocarbyl amine borates such as: . CHZCHZO .where R and x are de?ned as above. 45 The borated derivatives are conveniently produced RN B~O—CH2 by the reaction of the selected mixture of compounds CHZCHZO (CI-10H); with, for example, boric acid, in the presence of a suit CHZOCR able solvent or solvents at temperatures ranging from II about 110° C. to about 280° C. Speci?c reaction condi tions and molar equivalents vary with the various reac tants and can be readily determined by one of ordinary or skill in the art. Besides direct treatment with boric acid CHZCHZOH other boration procedures several of which are well RN OCH; known in the art can
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