United States Patent (19) 11) 4,406,802 Horodysky et al. 45) Sep. 27, 1983

(54) FRICTION REDUCING ADDITIVES AND 56) References Cited COMPOSITIONS THEREOF U.S. PATENT DOCUMENTS 3,009,791 ll/1961 Emrick ...... 44/76 X (75) Inventors: Andrew G. Horodysky, Cherry Hill; 3,303,208 2/1967 Liao ...... 44/76 X Joan M. Kaminski, Clementon, both 3,445,498 5/1969 Cyba. 252/49.6 X of N.J. 3,505,226 4/1970 Cyba. ... .252/49.6 3,533,945 10/1970 Vogel ...... 252/49.6 3,544,614 12/1970 Schwartz 252/49.6 X 73 Assignee: Mobil Oil Corporation, New York, 3,560,386 2/1971 Cyba...... 252/49.6 N.Y. 4,022,713 5/1977 Waldstein ...... 252/389 R Primary Examiner-W. J. Shine Attorney, Agent, or Firm-Alexander J. McKillop; (21) Appl. No.: 259,219 Michael G. Gilman; Howard M. Flournoy (57) ABSTRACT Filed: Apr. 30, 1981 (22) Mixed borated alcohol-amines, alcohol-amides, alcohol ethoxylated amines, alcohol-ethoxylated amides, al (51) Int. Cl...... C10M 1/20; C10M 1/32; cohol-hydroxyester, alcohol-imidazolines and alcohol ClOM 1/54 hydrolyzed imidazolines and mixtures thereof are effec (52) U.S. C...... 252/49.6; 44/76; tive multifunctional additives when incorporated into 252/389 R; 252/400 R various organic media. 58 Field of Search ...... 252/49.6, 389 R, 400 R; 44/76; 568/1 12 Claims, No Drawings 4,406,802

FRCTION REDUCING ADDITIVES AND ROH COMPOSITIONS THEREOF where R may contain any desirable number of carbon BACKGROUND OF THE INVENTION 5 atoms based on such factors as oil solubility; however, R usually will contain from about 10 to about 30 carbon 1. Field of the Invention atoms and is an alkyl or substituted alkyl group which This invention relates to lubricant additives and com may be primary, secondary or tertiary, straight-chain, positions thereof and, more particularly, to lubricant compositions comprising oils of lubricating viscosity or branched or cyclic, it may contain one or more double greases prepared therefrom containing a minor friction 10 bonds, halogen or one or more sulfur atoms or an aro reducing amount of certain borated mixed alcohols, matic ring. Examples include such as decyl alcohol, amides, amines and esters. dodecyl alcohol, oleyl alcohol, stearyl alcohol, p-nitro 2. Description of the Prior Art benzyl alcohol, ethyl-octyl alcohol and mixed C12-C1s Many means have been employed to reduce overall linear alkanols. Alcohols having from about 12 to 24 friction in modern internal combustion engines, particu 15 carbon atoms are particularly useful. Particularly pre larly automobile engines. The primary reasons are to ferred are C10-C15 linear alkanols and C10-C12 branched reduce engine wear, thereby prolonging engine life and alkanols such as 2-ethyl-octanol and C15 alcohols such to reduce the amount of fuel consumed by the engine. as oleyl alcohol and stearyl alcohol. Many of the solutions to reducing fuel consumption The generalized structure of the hydroxyalkyl or have been strictly mechanical, as for example, setting 20 hydroxyalkenyl hydrocarbyl amides useful herein is: the engines for a leaner burn or building smaller cars O and smaller engines. However, considerable work has 2 been done with lubricants, mineral and synthetic, to R-C N / enhance their friction properties by modifying them 25 N with friction reducing additives. N Certain alcohols, mixtures of alcohols and other or (CH2CH2O).H ganic compounds have been used as intermediates in the manufacture of a variety of lubricant additives. How where R is as described above. Examples include bis(2- ever, the use of alcohols themselves, for example, has 30 hydroxyethyl) oleamide, bis(2-hydroxyethyl) cocoa not been widespread as engine oil additives because of mide, bis(2-hydroxyethyl) soyamide, bis(2-hydrox potential oxidative and thermal instability and volatility yethyl) octadecylamide, polyoxyethylene (5) oleamide, difficulties. It has now been found that certain borated polyoxyethylene (4) cocoamide, polyoxyethylene (5) mixed alcohols, amides, amines and hydroxy esters pro soyamide, etc. x and y may be the same or different and vide friction reducing characteristics that non-borated 35 each is from 1 to about 10, however, the sum of x and y compositions lack; in addition, the borated mixed deriv must always be 2 or greater. Propoxylated amides could atives improve oxidative and thermal stability, volatility also be used. and bearing corrosion inhibiting properties. These bo The generalized structure of the amines before bora rated mixed compositions are, to the best of applicants' tion is: knowledge, novel and have not been used as friction 40 reducing or multifunctional additives suitable for use in lubricating compositions and in fuels such as in gasoline, diesel fuel, jet fuel, etc. to improve fuel economy. The subject mixed borated compositions perform better than where R is as described above. Both saturated and un mixtures of individual borated materials, e.g., borated 45 saturated amines can be used; diamines and polyamines mixed oleyl amine and oleyl alcohol outperforms a are also useful. Examples include stearyl amine, cocoa mixture of borated oley alcohol and borated oley mine, laurylamine, soyamine, N-oleyl. 1,3-propylenedia a1e. mine, oleyl amine, aniline and dinitrophenylamine. R as SUMMARY OF THE INVENTION 50 stated hereinabove with respect to both the amides and This invention is directed to novel additive com the amines disclosed herein is as defined herein above. pounds, i.e., borates of mixed alcohols, amides, amines, The generalized structure of the hydroxyalkyl or and hydroxy esters, ethoxylated amines, and ethoxyl hydroxyalkenyl hydrocarbyl amines suitable for use in ated amides and mixtures thereof such as mixed alcohol, the present invention is: amine borates, mixed alcohol, and ethoxylated amine 55 borates. In addition to these novel compounds the in vention is also directed to lubricant compositions hav ing reduced friction containing such compounds and to a method of reducing fuel consumption in internal com bustion engines by treating the moving surfaces thereof 60 with said compositions. Further, as noted hereinabove and as stated hereinabove x and y may be the same or the novel compounds referred to also possess significant different and each is from 1 to about 10 and the sum of antioxidant characteristics and bearing corrosion inhib x and y must be 2 or greater. iting properties. Examples are bis(2-hydroxyethyl) oleylamine, bis(2- 65 hydroxyethyl) soyamine, bis(2-hydroxyethyl) cocoa DESCRIPTION OF SPECIFIC EMBODIMENTS mine, bis(2-hydroxyethyl) octadecylamine, polyoxyeth The generalized structure of the alcohols before bora ylene (5) oleylamine, polyoxyethylene (5) soyaamine, tion is: polyoxyethylene (4) cocoamine, etc. - 4,406,802 3 4 The generalized structure of the hydroxyesters are erally found in the non-mixed borated materials and to exemplified by the following general structure: an even greater degree than the individual borated ma terials. That is, the borated mixed materials perform in R O N a far superior manner to an equivalent physical mixture C-O-C-R of each specific borated material. Further, the higher 1 molecular weight borates have increased resistant to R (HoH), hydrolysis and retain their friction reducing characteris O tics even in the presence of water at elevated tempera where R is a hydrocarbyl group having from about 10 tures. to about 30 carbon atoms; said hydrocarby moiety may be alkyl, straight or branched, cyclic or substituted and Exemplary mixed borates so prepared are mixed al may contain one or more double bonds, halogen or one cohol-amine borates such as: or more sulfur atoms or aromatics rings; R = CH2OH, 15 CH3 or H; R = CH2OH or H and y is from i to about 5. The hydroxy esters may be made by the reaction of polyhydroxy alcohols with organic acids. For example, glycerol and oleic acid are used in the preparation of N R" / glycerol monooleate. Thioglycerol hydroxyesters can 20 also be used. The hydroxy esters must contain at least one free where a and b = 1 or 2 c = 0, or 1, R'' and R' have from hydroxyl group but may contain two or more. The about 10 to about 24 carbon atoms or can be H. hydroxy esters may also contain one ester group (as in glycerol monooleate) or more (as in glycerol dioleate). The structure of mixed alcohol-ethoxylated amide The esters can be used in pure form, or preferably in 25 borates can be generalized as follows: mixtures such as mixtures of glycerol mono- and diole ate. Sorbitan hydroxyesters and hydroyesters prepared (O-CH2CH2) O from trimethylolpropane and pentaerythritol are also useful, e.g., sorbitan monooleate, trimethylolpropane 30 monooleate, trimethylolpropane dioleate, pentaerythri (O-CH2CH2) tol dioleate monolaurate and the like. Also useful are hydroxyalkyl or hydroxyalkenylalkyl and various similar or related ring-opened borate struc or alkenylimidazolines and/or hydrolysis products of tures where R, R', x, y are as defined above or mixed the imidazoline. The general structure of such com alcohol-ethoxylated amines borates such as: pounds can be as described below:

(O-CH2CH2). 40

and various ring-opened structures where x, y, R and where R has from about 10-30 carbon atoms and may 45 R" are as defined above. be alkyl or alkenyl, arylalkyl, alkyl aryl, etc. and X is The structure of mixed alcohol-hydroxyester borates from 1 to about 5. Their respective ring-opened hydro can have the general structures: lysis products are made by treatment of the above described imidazolines with at least molar amounts of Water. SO sh-o--R The borated derivatives can be conveniently pro OCH O o duced by the reaction of selected mixtures of the com / (R"-O)-B pounds in accordance herewith with boric acid in a N suitable solvent or solvents at temperatures ranging OCH2 from about 10 C. to about 280 C. Specific reaction 55 conditions and molar equivalents vary with the reac tants and can be readily determined by one of ordinary O skill in the art. Besides direct treatment with boric acid O R'O CH2OC-R I N several other boration procedures which are well CH2OCR Bio-O-o-CH known in the art can be used, e.g., transesterification 60 / with a trialkyl borate such as tributyl borate. In any (R'O)-B-OCH or HO R'O event the boration procedure is most conveniently a (R"O)-B-OCH2 N one-pot, one-step process. B-O-CH2 The borated mixed materials are much more effective / friction reducers than their non-borated counterparts or 65 HO physical mixtures of the individual borated materials. As noted above the borated mixed materials also possess For example, mixed borate trimethylolpropane hy antioxidant and corrosion inhibiting properties not gen droxyesters have the following generalized structures: 4,406,802 6 glycerol monooleate used in the examples set out below O O were obtained commercially. CH2OCR (HoCR EXAMPLE 5 chi-crcho-B-OR). or CH-i-Cho-BOR), or Borated Mixed Oleyl Alcohol and Oley Amine CH2O CHO-B(OR") Approximated 134 g of oleyl alcohol and 133 g of oleyl amine were charged to a reactor equipped with a O thermometer, an overhead stirrer, and a Barrett trap CH2OCR OR' and condenser for azeotropic distillation. Approxi / O CH-C-CH2O-B mately 11 1 g of n-butanol and 20.6 g boric acid were N also charged to said reactor. The reaction solution was OH heated to 110° C. at which time water began to distill OR" / over. In 5 hours 16.8 cc H2O were removed as the CH2O-B 15 reaction temperature increased to 160° C. The solvent was removed by vacuum distillation, and the borated OH product was filtered over diatomaceous earth to yield a Also included in the present invention are mixed alco clear, brown fluid. hols and imidazoline borates and mixed alcohol-hydro EXAMPLE 2 lyzed imidazoline borates. 20 The amount of these novel additives required to be Ring-Opening Hydrolysis of effective in lubricant compositions ranges from about 1-(2-Hydroxyethyl)-2-Heptadecenylimidazoline 0.1 to about 10% by weight of the total lubricant com A mixture of 1-(2-hydroxyethyl)-2-hep position. Preferred is from about 0.5 to 5 wt.%. The tadecenylimidazoline (40 g), water (9.4 g), and ethanol additives of this invention may also be used in combina 25 (9.6 g) was stirred and heated at 90° C. for 3 hours. The tion with other systems having additives in conven water and ethanol were removed by high speed rotary tional amounts for their known purpose. The use of evaporation, and the resulting product was a golden additive concentrations of these borated materials in waxy solid. The infrared spectrum of the product con premium quality automotive and industrial lubricants tained a strong carbonyl absorption band in the further improves upon such fluids' fuel economy char 30 acteristics. The non-metallic compositions described 1640-1650 cm-1 region and showed no characteristic herein are useful, therefore, at moderate concentrations imidazoline carbon-nitrogen imido band at 1600 cm, and do not contain any potentially undesirable phospho thereby, indicating complete ring-opening of the start rus, corrosive sulfur or metallic salts. ing imidazoline. The lubricants contemplated for use herein include 35 EXAMPLE 3 both mineral and synthetic hydrocarbon oils of lubricat ing viscosity, mixtures of mineral and synthetic oils, and Borated Mixed C12-C15Alkanols and Hydrolyzed greases prepared therefrom. The synthetic hydrocarbon 1-(2-Hydroxyethyl)-2-Heptadecenylimidazoline oils include long chain alkanes such as cetanes and ole-, Approximately 103 g of C12-C15 alkanols and 184 g of fin polymers such as trimers and tetramers of octene and hydrolyzed 1-(2-hydroxyethyl)-2-hep decene. These synthetic oils can be mixed with other tadecenylimidazoline (hydrolyzed as described in Ex synthetic oils which include (1) ester oils such as penta ample 2) were charged to a reactor equipped with a erythritol esters of monocarboxylic acids having 2 to 20 thermometer, an overhead stirrer, and a Barrett trap carbon atoms, (2) polyglycol ethers, (3) polyacetals and and condenser for azeotropic distillation. Approxi (4) siloxane fluids. Especially useful among the syn 45 mately 111 g n-butanol and 31 g boric acid were also thetic esters are those made from polycarboxylic acids charged to said reactor. The reaction solution was and monohydric alcohols. More preferred are the ester heated to 110 C. at which time water began to distill fluids made from pentaerythritol, and an aliphatic over. In 5 hours 15 cc H2O were removed as the reac monocarboxylic acid containing from 1 to 20 carbon tion temperature increased to 163 C. The solvent was atoms, or mixtures of such acids. 50 removed by vacuum distillation, and the borated prod Lubricant compositions containing the novel friction uct was filtered over diatomaceous earth to yield a reducing additives of the present invention can also clear, brown fluid. include additive concentations of ashless dispersants, detergents, inhibitors, antiwear, extreme pressure, anti EXAMPLE 4 foam and viscosity improving additives and the like 55 Borated Mixed Oleyl Alcohol and Bis(2-hydroxyethyl) without significantly affecting the performance of the Oleanide additives in accordance with the invention. The novel friction reducers can also be advantageously used in Approximately 36 g bis(2-hydroxyethyl) oleamide internal combustion engine fuels, effective friction re (made by the reaction of oleic acid and diethanolamine) ducing amounts vary, from about 2 to about 1000 lbs. 60 and 53 goley alcohol were charged to a 500 Ml glass per thousand barrels of fuel and preferably from about reactor fitted with an agitator, Dean-Stark tube and 50 to about 300 lbs. per thousand depending, inter alia, nitrogen sparge to exclude air. Approximately 10 g on the specifications of the particular fuel. w boric acid and 60 g toluene solvent were added. The Having described the invention in general terms, the reactants were heated to 195 C. over a period of 4 following are offered as specific illustrations thereof. 65 hours during which time 83 g water were removed by Oleyl alcohol, oleylamine, 1-(2-hydroxyethyl)-2-hep azeotropic distillation. The solvent was removed by tadecenyl imidazoline, C12-C15 alkanols, bis(2-hydrox vacuum distillation. The borated product was filtered yethyl) oleamide, bis(2-hydroxyethyl) oleamine, and over diatomaceous earth to yield a clear, orange fluid. 4,406,802 7 8 temperature for a few minutes. A plot of coefficients of EXAMPLE 5 friction (Uk) over a range of sliding speeds, 5 to 40 fpm Borated Mixed Oleyi Alcohol and Glycerol (25-195 rpm), is obtained. A minimum of three measure Monooleate ments is obtained for each test lubricant. Then, the test Approximately 165 g glycerol monooleate (60/40 5 lubricant and specimens are heated to 250 F., another mixture glycerol monooleate/glycerol dioleate) and 134 set of measurements is obtained, and the system is run goleyl alcohol were charged to a one liter glass reactor for 50 minutes at 250 F., 500 psi, and 40 fpm sliding equipped as in Example 4. Approximately, 25 g boric speed. Freshly polished steel specimens are used for acid and 50g toluene solvent were added. The reactants each run. The surface of the steel is parallel ground to 6 were heated up to 200° C. over a period of 6 hours after O to 8 microinches. The percentages by weight are per which time water evolution via azeotropic distillation centages by weight of the total lubricating oil composi ceased. The solvent was removed by vacuum distilla tion, including the usual additive package. The data are tion and the borated product was filtered over diatoma percent decrease in friction according to: ceous earth to yield a clear, amber fluid. 15 EXAMPLE 6 (Uk of oil alone) - (Uk of Additive plus oil) Borated Mixed Alcohols and Ethoxylated Amines (Uk of oil alone) Approximately 1450 grams of oley alcohol, 1900 Thus, the data are expressed in this form in the Table grams of bis(2-hydroxyethyl) oleylamine, 410 grams of below. boric acid, 40 grams of butanol and 200 grams of tolu 20 ene were charged to a 5 liter reactor equipped with an TABLE 1 agitator and Dean-Stark tube. After a 7 hour reaction FRICTION CHARACTERISTICS period at temperatures up to 170° C., water evolution Reduction or % terminated. Approximately 73 grams of mixed linear Additive Change in Coefficient alkanols, obtained commercially and having an average 25 Conc., of Friction molecular weight of 208 and an hydroxyl number of 270 Example No. Wi. 2, 5 ft./min. 30 ft./min. (approximately 80% of the alcohols were linear alco Base Oil SAE SW-20 O - - hols with the following carbon number distribution: Example 1: Borated mixed 4. 43 31 17.7% C12, 30% C13, 28% C14 and 24% C15) were 30 oley alcohol and oleylamine 'rt added, and the mixture heated at 170 for an additional Example 3: hour. The solvents were removed by vacuum distilla Borated mixed 4. 35 30 tion and the crude product filtered over diatomaceous C2-C15 alkanols and earth to yield an orange fluid. hydrolyzed 1-(2-hydroxyethyl) Certain of the borated materials were then dissolved 2-heptadecenylimidazoline in a SAE5W-20, automotive engine oil containing a 35 Example 4: Borated mixed 4. 30 25 standard additive package as described above and then oley alcohol and bis(2- subjected to testing in the Low Velocity Friction Appa hydroxyethyl) oleamide ratus Test described below. Test results are reported in Example 5: Table i, below. Borated mixed 4. 35 22 oleyl alcohol and glycerol Low Velocity Friction Apparatus (LVFA) monooleate The Low Velocity Friction Apparatus (LVFA) is Example 6: used to measure the friction of test lubricants under Borated mixed 4. 32 22 oley alcohol, mixed C2-C1s 2 36 28 various loads, temperatures, and sliding speeds. The alkanols and bis(2-hydroxy- 3. 24 LVFA consists of a flat SAE 1020 steel surface (diam. 45 ethyl) oleylamine 1.5 in.) which is attached to a drive shaft and rotated over a stationary, raised, narrow ringed SAE 1020 steel surface (area 0.08 in.2). Both surfaces are submerged in Bearing corrosion inhibiting properties of representa the test lubricant. Friction between the steel surfaces is tive compounds were tested via copper corrosivity measured as a function of the sliding speed at a lubricant 50 tests, ASTM D 30-6, ASTM D 130-9. The results are temperature of 250 F. The friction between the rubbing reported in Table 2, below. surfaces is measured using a torque arm strain gauge TABLE 2 system. The strain gauge output, which is calibrated to COPPER STRIP CORROSIWTY CHARACTERISTICS be equal to the coefficient of friction, is fed to the Y axis ASTM ASTM of an X-Y plotter. The speed signal from the tachome 55 Concen- D 130-6 D-130-9 ter-generator is fed to the X-axis. To minimize external tration in 250 F., 210 F., friction, the piston is supported by an air bearing. The Example No. 200 SPN 3 hrs. 6 hrs. normal force loading the rubbing surfaces is regulted by Example 1: - air pressure on the bottom of the piston. The drive Borated mixed oleyl 3 1A 1B system consists of an infinitely variable-speed hydraulic 60 alcohol and oleylamine 1A B transmission driven by a HP electric motor. To vary Example 3: - the sliding speed, the output speed of the transmission is Borated mixed C2-C5 3 1A A alkanols and hydrolyzed 1-(2- A A. regulated by a lever cam-motor arrangement. hydroxyethyl)-2-heptadecenyl Procedure inidazoline 65 Example 4: The rubbing surfaces and 12-13 ml. of test lubricant Borated mixed 3 1A 1A are placed on the LVFA. A 500 psi load is applied, and oley alcohol and bis(2- B 1A the sliding speed is maintained at 40 fpm at ambient hydroxyethyl) oleamide 4,406,802 9 10 TABLE 2-continued TABLE 3-continued CATALYTICOXIDATION TEST COPPER STRIP CORROSIVITY CHARACTERISTICS 40 hours at 325 F. ASTM ASTM %. Increase in Concen- D 30-6 D-130-9 5 Addi- Viscosity of tration in 250 F., 210 F., tive Lead Oxidized Oil Neut. conc., Loss, Using KV G. Num Example No. 200 SPN 3 hrs. 6 hrs. Example No. wt.% mg. 100 C. ber Example 5: Borated mixed oley 3 O.O 15 1.96 Borated mixed oleyl 3 1A 1A 10 alcohol, mixed C2-C15 1 0.0 13 1.43 alcohol and glycerol monooleate 1 1A A alkanols and bis(2-hydro Example 6: ethyl) oleylamine Borated mixed oleyl 3 1A 1A alcohol, mixed C2-C5 alkanols 1A 1A It can be clearly seen that these mixed borates impart and bis(2-hydroxyethyl) 15 significant friction reducing, corrosion inhibiting, and oleylamine antioxidant characteristics to oleagenous lubricant com positions. It is understood by one of ordinary skill in the art that Certain of the examples were also tested for their modifications and variations from the exemplary mate antioxidation characteristics in the B-10 Catalytic Oxi rial disclosed herein can be readily made and is within dation Test at 325 F. for 40 hours. The test lubricant 20 the scope of this specification. composition is subjected to a stream of air which is We claim: 1. A lubricant composition comprising a major pro bubbled through the composition at a rate of 5 liters per portion of an oil of lubricating viscosity or grease pre hour at 450 F. for 24 hours. Present in the composition pared therefrom and a minor effective amount of a comprising a 200 seconds paraffinic neutral oil in addi 25 multi-functional additive compound having friction tion to the additive compound were metals commonly reducing and oxidation and corrosion inhibiting charac used as materials to construct engines namely: teristics selected from the group consisting of borated (a) 15.6 sq. in. of sand-blasted iron wire; mixed C12-C15 alcohols and hydrolyzed 1-(2-hydroxye (b) 0.78 sq. in. of polished copper wire; thyl)-2-heptadecenylimidazoline; and borated mixed 30 oleyl alcohol and glycerol monooleate or mixtures of (c) 0.87 sq. in. of polished aluminum wire; and said borated compounds prepared by borating under (d) 0.107 sq. in. of polished lead surface. suitable boration conditions selected mixtures of appro The test results are reported below in Table 3. priate compounds in suitable solvent or mixtures TABLE 3 thereof at temperatures of from about 110 to 280 C. 35 said compounds having one or more alkyl or substituted CATALYTICOXIDATION TEST alkyl groups attached thereto, and where said group is 40 hours at 325 F. straight or branched chain, cyclic or contains one or % increase in more double bonds, halogen or one or more sulfur Addi- Viscosity of 40 atoms or aromatic rings and said group having from tive Lead Oxidized Oil Neut. about 10 to about 30 carbon atoms. conc., Loss, Using KV G2) Num 2. The composition of claim 1 wherein the additive is Example No. wt.% mg. 100 C. ber borated mixed C12-C15 alcohols and hydrolyzed 1-(2- Base oil 200' - 1.2 67 3.62 hydroxyethyl)-2-heptadecenylimidazoline. paraffinic neutral 45 3. The composition of claim 1 wherein the additive is lubrication oil borated mixed oley alcohol and glycerol monooleate. Example 1: 4. The composition of claim 1 wherein said oil is Borated mixed oleyl 3 0.0 32 2.47 selected from mineral oils, synthetic oils and mixtures alcohol and oleylamine 1 0.0 14 3.48 thereof. Example 3: 50 5. The composition of claim 1 wherein said oil is a Borated mixed C2-C15 mineral oil. alkanols and hydrolyzed 3 4.6 15 2.27 6. The composition of claim 1 wherein said oil is a -(2-hydroxyethyl)- l 0.0 14 2.2 synthetic oil. 2-heptadecenyl imidazoline 7. The composition of claim 1 wherein said oil is a Example 4: 55 mixture of synthetic oils and/or mineral oils. Borated mixed 3 O.O 20 2.55 8. The composition of claim 1 wherein said major oley alcohol and proportion comprises a grease. bis(2-hydroxyethyl) 9. A borated additive as described in claim 2. oleamide l 1.0 17 2.68 10. A borated additive as described in claim 3. Example 5: 60 11. The composition of claim 1 wherein said boration Borated mixed oleyl 3 0.0 32 2.40 is via boric acid. alcohol and glycerol 12. The composition of claim 1 wherein the said bora monooleate 1 0.0 21 1.83 tion is via transesterification with a trialkyl borate. Example 6: ck :k sk sk 22 65