FR2541685A1 - LUBRICATING OIL COMPOSITION CONTAINING GLYCEROL BORATE FATTY ACID ESTER SUCCINIMIDE COMPLEX - Google Patents

Abstract

THE INVENTION CONCERNS LUBRICATING OILS. IT HAS MORE PARTICULARLY DEALED WITH A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR QUANTITY OF A LUBRICATING OIL WITH A VISCOSITY AND AN EFFECTIVE QUANTITY TO REDUCE THE FRICTION OF A REACTION-PREPARED COMPLEX: WITH AN ACID ESTER FAT BORATE GLYCEROL OR MIXTURES OF SUCH ESTERS; AND B OF AN OIL SOLUBLE ALKYL- OR ALCENYLSUCCINIMIDE. APPLICATION TO REDUCING FUEL CONSUMPTION BY AN INTERNAL COMBUSTION ENGINE.

Description

The present invention relates to the product obtained by reaction of esters

of borated fatty acids

  glycerol with a succinimide and the use of

  in lubricating compositions.

  Given the crisis of dwindling fossil fuel reserves and the rapid rise in fossil fuel prices, many

  have been deployed to reduce the amount of fuel

  consumed by motor vehicle engines, etc. It is therefore urgent to find lubricants that reduce the overall friction in the engine, so as to reduce energy requirements

of the motor.

  U.S. Patent No. 4,201,684 discloses lubricating oils containing amides, esters, or ester-amides of sulfur-containing fatty acids of alkoxylated amines, which reduce friction between sliding metal surfaces in combustion engines.

internal combustion.

  U.S. Patent No. 4,161,486 teaches lubricating oils containing certain acid esters having double bonds or the dimer or trimer of these acid esters. internal combustion are claimed by the use of oils

  lubricating in the crankcase.

  U.S. Patent No. 3,151,077 teaches the use of borated monoacylated trimethylolalkanes as fuel additives and engine lubricating oil. The additives are believed to be able to reduce the incidence of surface ignition in a vehicle. internal combustion engine and to inhibit the accumulation

deposits in the carburetor.

  U.S. Patent No. 2,795,548 discloses the use of lubricating oil compositions

  containing a borated glycerol mono-oleate.

  oil are used in the crankcase of an internal combustion engine to reduce the oxidation of

  oil and corrosion of metal parts of the engine.

  The use of borated fatty acid esters of glycerol in lubricating oils poses a problem since these esters are sensitive to moisture and

  hydrolysis rapidly Hydrolysis leads to the formation of

  The glycerol oleate which is generated as a consequence of the hydrolysis causes problems of corrosion of the bearings and / or the formation of a haze and / or precipitate which must be removed by filtration before use. precipitation problems in the presence of some zinc dihydrocarbyldithiophosphonates and

some metal phenates.

  The Applicant has just discovered that the borated fatty acid esters of glycerol could be stabilized against hydrolysis by complexing said glycerol esters with an alkenyl or alkyl-mono or bissuccinimide. The Applicant has discovered the very important fact that the lubrication of the crankcase of an internal combustion engine with a lubricating oil containing the reaction product of a borated fatty acid ester of glycerol and a succinimide reduced the consumption.

engine fuel.

  According to the present invention, there are provided lubricating oils which reduce friction between sliding metal surfaces and which are

  particularly useful in the engine crankcase

  internal combustion The reduction of friction results from the addition to the lubricating oil of small quantities of a complex prepared by reaction of an acid ester

  borated fat of glycerol and an alkyl or alkenyl mono-

or bis-succinimide.

  Accordingly, the present invention relates to a lubricating oil composition comprising an oil of lubricating viscosity and an amount effective to reduce the friction of a complex prepared by reacting (a) a fatty acid ester. borate glycerol or mixtures thereof and (b) a soluble alkyl or alkenyl mono or bis-succinimide

in the oil.

  Other additives may also be present in the lubricating oil to achieve a balance

  correct properties such as dispersion, inhibition

  corrosion, wear and oxidation, which are decisive for the proper functioning of a

internal combustion engine.

  In addition, according to the invention, there is provided a method for reducing the consumption of a

  fuel from an internal combustion engine by

  The motive surfaces of said engine with the lubricating oil composition described above have been observed in particular in engine tests fuel consumption improvements ranging from 2 to 3% on average This improvement in the economy of fuel can be obtained both in compression ignition engines, ie diesel engines,

  only in spark-ignition engines, that is,

say gasoline engines.

  The borated fatty acid esters of glycerol are prepared by borating a glycerol fatty acid ester with boric acid, with removal of the reaction water. The boron is advantageously present in an amount sufficient for each boron reacts with 1.5 to 2.5 hydroxyl groups present-in

the reaction mixture.

  The reaction can be carried out at a temperature in the range of 60 to 1350 ° C., in the absence or in the presence of any suitable organic solvent such as methanol, benzene, xylenes, toluene, neutral oil, etc. The fatty acid esters of glycerol can be prepared by various methods well known in the art. Many of these esters such as glycerol monoester and glycerol ester of tallow fatty acid are produced on an industrial scale. Esters that can be used in the present invention

  are oil-soluble and are advantageously

  trimmed with C 8 to C 22 fatty acids or mixtures of these acids; such as those found in natural products The fatty acid may be saturated or unsaturated Certain compounds found in acids from natural sources may contain licanic acid which contains a keto group. Most preferred are those which have the formula R-COOH wherein R is alkyl or alkenyl. The use of a glycerol fatty acid monoester is recommended; However, it is possible to use mixtures of monesters and diesters. Any mixture of monoester and diester advantageously contains at least

  minus 40% monoester Mixtures of mono and.

  glycerol diesters contain very advantageously

  60% by weight of the monoester For example, the mono-

  Commercial glycerol oleate contains a mixture of 45 to 55% by weight of monoester and 55 to 45% of diester. Preferred fatty acids are oleic, stearic, isostearic, palmitic, myristic, palmitoleic, linoleic, lauric, linolenic, and

  eléostéarique, and the acids derived from natural products

  such as tallow, palm oil, olive oil, peanut oil, corn oil, beefstooth oil, etc. A particularly preferred acid is the acid

oleic.

  The oil-soluble alkenyl or alkyl mono or bis-succinimides which are used in the present invention are generally known as lubricating oil detergents and are described in US Pat. Nos. 2,992,708, N 3,018,291,

  N 3 024 237, N 3 100 673, N 3 219 666, N 3 172 892

  and N 3 272 746 Alkenyl succinimides are the reaction product of a substituted succinic anhydride

  polyolefinic compound with an amine, preferably a poly-

  alkylene polyamine Polyolefin-substituted succinic anhydrides are obtained by reacting a polyolefinic polymer or a derivative thereof with maleic anhydride. The succinic anhydride thus obtained is reacted with the amine compound. The preparation of the alkenyl succinimides has been described. Many times in the prior art reference is made, for example, to U.S. Patent Nos. 3,390,082, 3,219,666 and N 3,172,892. The reduction of anhydride

  alkenyl-substituted succinic acid gives the alkyl derivative

  A product mainly comprising mono or bissuccinimide may be prepared by

  adjustment of the molar ratios of the reactants.

  Thus, for example, if one mole of amine is reacted with one mole of the alkenyl or alkyl substituted succinic anhydride, the monosuccinimide predominant product is prepared if two moles of the anhydride are reacted. succinic per mole of polyamine, is prepared

bis-succinimide.

  Particularly advantageous results are obtained with the lubricating oil compositions of the invention when the alkenyl succinimide is a polyisobutene substituted succinic anhydride of a

polyalkylenepolyamine.

  The polyisobutene from which the polyisobutene-substituted succinic anhydride is obtained is produced by isobutene polymerization and its composition.

  can vary widely The average number of carbon atoms

  bone can range from -30 or less than 30 to 50 or more

  250, which gives an average number of the molecular weight

  Preferably, the average number of carbon atoms per molecule of polyisobutene is from about 50 to about 100, the polyisobutenes having a number average molecular weight of about 600 to about 100. about 1500 The average number of carbon atoms per molecule of polyisobutene ranges from about 60 to about 90 and the average

  in number of the molecular weight is from about 800 to 1300.

  The polyisobutene is reacted with maleic anhydride according to methods well known for

  form the polyisobutene substituted succinic anhydride.

  In the preparation of alkenyl succinimide, the substituted succinic anhydride is reacted with a polyalkylene polyamine to obtain succinimide

  corresponding to each alkylene radical of the polyalkylene

  polyamine usually comprises up to about 8 carbon atoms The number of alkylene radicals can range up to about 8 The alkylene radical is exemplified by alkylene, propylene, butylene, trimethylene,

  tetramethylene, pentamethylene, hexamethylene, octa-

  methylene, etc. The number of amino groups is in general but not necessarily one unit higher than the number of alkylene radicals present in the amine, that is, if a polyalkylene polyamine contains 3 radicals

  alkylene, it usually has 4 amino groups.

  The number of amino groups can reach about 9.

  Preferably, the alkylene radical contains about 2 to about 4 carbon atoms and all amino groups are primary or secondary. In this case, the number of amino groups exceeds the number of alkylene groups.

  Polyalkylenepolyamine contains

  3 to 5 amino groups Representative examples of the polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine,

  propylenediamine, tripropylenetetramine, tetra-

  ethylenepentamine, trimethylenediamine, penta

  ethylenehexamine, di- (trimethylene) triamine, tri (hexamethylene) tetramine, etc. Other advantageous amines to be used for preparing the alkenyl succinimide which can be used

  in the present invention include cyclic amines

  such as piperazine, morpholine and dipiperazine. The alkenyl succinimides used in the compositions of the present invention advantageously have the following formula: ## STR2 ##

CH 2-C% -

2 A

  wherein: R 1 represents an alkynyl group, preferably a predominantly saturated hydrocarbon prepared by polymerization of aliphatic monoolefins R 1 is preferably prepared from isobutene and has an average number of carbon atoms and a number average of the weight molecular as indicated above; b the "alkylene" radical represents a predominantly hydrocarbyl group containing up to about 8 carbon atoms and preferably containing about 2 to 4 carbon atoms as described above; c A represents a hydrocarbyl group, a

  amino-substituted hydrocarbyl group or hydrogen.

  The hydrocarbyl group and the amino-substituted hydrocarbyl groups are generally the alkyl analogues

  and amino-substituted alkyls of the alkyl radicals

  described above A preferably represents hydrogen; d N is an integer of about 1 to 10

and in particular from about 3 to 5.

  The alkenyl succinimide is present in the lubricating oil compositions of the invention in an amount effective to stabilize the acid esters.

  borated fat against hydrolysis and to act as a

  persant and to prevent the deposition of impurities

  in the oil during engine operation.

  The complex whose exact nature is not known can be formed by reacting the borated fatty acid esters of glycerol and succinimide together, without diluent, at a temperature above the melting point of the mixture of reactants and below the melting point of the reaction mixture. decomposition temperature, or in a diluent

  wherein both reactants are soluble.

  For example, the reactants can be combined in the correct ratio in the absence of a solvent to form a homogeneous product that can be added to the oil, or the reactants can be combined in the correct ratio in a solvent. such as toluene or chloroform, the solvent is removed and the complex thus formed can be added to the oil. Alternatively, the complex can be prepared in a lubricating oil in the form of a concentrate containing about 10 to 90% by weight of the complex, this concentrate can be added

  in quantities appropriate to the lubricating oil in the

  which it should be used, or else the complex can be prepared directly in the lubricating oil in

which one should use it.

  The diluent is advantageously inert vis-à-

  react reactants and formed products and is used in sufficient quantity to ensure the

  solubility of the reactants and to allow agri-

effective mixing.

  The complex preparation temperatures may be in the range of 25 to 200 ° C and in particular 25 to 100 ° C depending on whether the complex is prepared without diluent or in a diluent, i.e. can use lower temperatures when

serves as a solvent.

  The ratio of weight percent succinimide to borated fatty acid ester of glycerol to form the complex is in the range of 0.5: 1 to 3: 1, preferably 1: 1 to 2: 1. and it is especially equal to 1: 1 This latter ratio is recommended if the complex is prepared and / or stored without diluent or in the absence of solvent or lubricating oil and in the

weather conditions.

  The amount of additive required to effectively reduce friction in lubricating oil compositions can range from 0.3 to about 10% by weight of the total lubricating composition and the additive is advantageously present in the range of 1 to 5 % by weight Succinimide is present in the complex of the invention in an amount effective to stabilize the borated esters against hydrolysis and to allow the borated esters to function effectively as

friction reducing agents.

  Similarly, the succinimide in the complex acts as a dispersant and prevents the deposition of impurities

  formed in the oil during engine operation.

  In general, the complexes of the present invention can also be used in combination with other additive systems in conventional amounts.

for their known purpose of use.

  For example, for use in modern crankcase lubricants, the base composition described above is formulated with additional additives to create the necessary properties of stability, detergency, anti-wear dispersion.

and anti-corrosion.

  Consequently, according to another form of

  In accordance with the invention, the lubricating oils to which the complexes prepared by reaction of the borated fatty acid esters of glycerol and succinimides are added may contain an alkali metal or alkaline earth metal hydrocarbyl sulfonate, an alkali metal or alkaline phenate. -terrous and a dihydrocarbyldithiophosphate

Group II metal.

  Also, since the succinimides act as excellent dispersants, an additional amount of succinimides can be added to the lubricating oil compositions, in addition to the amounts added as a complex with the esters.

  borated fatty acids of glycerol The amount of

  nimides can reach about 20% by weight of

  total lubricating oils.

  The hydrocarbylsulfonates of alkali or alkaline earth metals can be petroleum sulfonates, synthetic alkylated aromatic sulfonates or aliphatic sulfonates such as those derived from polyisobutylene. One of the most important functions of sulfonates is their action. These sulphonates are well known in the prior art. The hydrocarbyl group must have a sufficient number of carbon atoms to make the sulphonate molecule soluble in the oil. The hydrocarbyl portion advantageously comprises at least

  20 carbon atoms and may be aromatic or aliphatic.

  However, it is usually alkylaromatic. Calcium sulfonates are very advantageously used.

  magnesium or barium which are aromatic.

  Some sulphonates are normally prepared by sulphate

  fraction of oil bearing groups

  aromatic compounds, usually mono or di-

  The other materials used to prepare these sulfonates include alkylated benzenes by synthesis and aliphatic hydrocarbons prepared by polymerization of a mono-olefin or a diolefin.

  for example a polyisobutenyl group prepared by poly-

  Isobutene Merification Metal salts are formed directly or by metathesis using

well known methods.

  The sulfonates can be neutral or overbased, with base numbers up to about 400 or more. Carbon dioxide and calcium hydroxide or oxide are the materials most commonly used to produce

  basic or overbased sulphonates can be used

  mixtures of neutral sulphonates

  The sulfonates are usually used in such a way that their amount represents 0.3 to 10% by weight of the total composition. Preferably, the neutral sulfonates are present in proportions of 0.4 to 5% by weight of the total composition and the sulfonates overbased renderings are present in proportion of 0.3

  at 3% by weight of the total composition.

  The phenates for use in the present invention are the conventional products which

  are the alkali metal or alkali metal salts

  of alkylated phenols One of the functions of

  nates is their action as a detergent and as a dispersant.

  Among other things, phenate prevents the deposition of

  formed during high-temperature operation.

  motor phenols may be monoalkylated

or polyalkylated.

  The alkyl portion of the alkylphenate is

  to give the phenate the solubility in oil.

  The alkyl portion can come from natural sources or

  Synthetic natural sources include hydro-

  petroleum carbides such as white oil and wax.

  Being derived from petroleum, the hydrocarbon portion is a mixture of different hydrocarbyl groups whose

  particular composition depends on the particular base oil

  The suitable synthetic sources include various commercially available alkenes and alkane derivatives which, when reacted with phenol, give an alkylphenol. Suitable radicals include butyl radicals, hexyl, octyl, decyl, dodecyl, hexadecyl, eicosyl, tricontyl, etc. Other suitable synthetic sources of alkyl include

  olefinic polymers such as polypropylene, poly-

  butylene, polyisobutylene, etc. The alkyl group may be a straight-chain or branched-chain, saturated or unsaturated group (if it is unsaturated it preferably contains no more than

  2 and generally no more than one unsaturated

  Alkyl radicals generally contain from 4 to 30 carbon atoms In general, when the phenol is monoalkylated, the alkyl radical must contain at least B carbon atoms. The phenate may be sulphidised if appropriate. It may be neutral and overbased and the latter case, it has a basicity index of 200 to 300 or more.

  Neutral and overbased phenates.

  The phenates are usually present in the oil in a proportion of from 0.2 to 27% by weight of the total composition. Preferably, the neutral phenates are present in a proportion of 0.2 to 9% by weight of the total composition and the phenates Overbased renderers are present in a proportion of from 0.2 to 13% by weight of the total composition. The overbased phenates are most preferably present in an amount of from 0.2 to 5% by weight of the total composition. Preferred metals

  are calcium, magnesium, strontium and barium.

  The alkylphenates of sulphurised alkaline earth metals are preferred. These salts are obtained by various

  processes, for example by treating the neutralization product

  Use of an alkaline earth base and an alkylphenol with sulfur Sulfur in the elemental form is advantageously added to the neutralization product and reacted at elevated temperatures to produce

  the sulphurated alkaline earth metal alkylphenate.

  If, during the neutralization reaction, more alkaline earth base is added than it was necessary to neutralize the phenol, we obtain

  a basic alkaline-earth metal sulphide alkylphenate.

  For example, reference is made to U.S. Patent No. 2,680,096. The basicity can be increased by adding

  from carbon dioxide to alkali metal alkylphenate

  basic earthy sulphide The alkaline earth metal base

  in excess can be added later in the sulphurization step.

  ration, but it is added advantageously at the same time as the alkaline earth base is added to neutralize

phenol.

  Carbon dioxide and calcium hydroxide or oxide are the materials most commonly used to produce the basic or

  "Overbased" means a process in which alkyls are

  basic alkaline sulphide phenates are produced by addition of carbon dioxide is described in the

  U.S. Patent No. 3,178,368.

  The Group II metal salts of di-

  Hydrocarbyl dithiophosphoric compounds are endowed with anti-wear, antioxidant and heat-stabilizing properties Group II metal salts of phosphorodithioic acids have already been described (see, for example, columns 6 and 7 of U.S. Patent No. 3,390 080 o on

  finds a general description of these compounds and of

  their preparation) Group II metal salts of dihydrocarbyldithiophosphoric acids useful in the

  lubricating oil composition of the invention contains

  Advantageously, about 4 to about 12 carbon atoms in each of the hydrocarbyl radicals and may be equal or different and of aromatic, alkyl or cycloalkyl nature. Preferred hydrocarbyl groups are alkyl groups containing from 4 to 8 carbon atoms and are represented by the groups butyl, isobutyl, sec-butyl, hexyl, isohexyl, octyl, 2-ethylhexyl, etc. Suitable metals for forming such salts include barium, calcium, strontium, zinc and cadmium, of which preference is given to zinc.

  The Group II metal salt of a dihydric acid

  drocarbyldithiophosphoric acid advantageously corresponds to the following formula r R 2 Os Sd

R 3 OX S-

2

  in which e R 2 and R 3 represent, independently, hydrocarbyl radicals as defined above and M 1 represents a metal cation of

  Group II as defined above.

  The dithiophosphoric salt is present in the lubricating oil compositions of the invention in an amount effective to inhibit wear and oxidation of the lubricating oil. The amount is from about 0.1 to about 4% by weight of the lubricating oil. the total composition, the salt being suitably present in an amount of from about 0.2 to about 2.5% by weight of the total lubricating oil composition The final lubricating oil composition usually contains 0.025 to 0.25% by weight phosphorus

  and preferably 0.05 to 0.15% by weight.

  The ready-to-use lubricating oil is single or multigrade Multigrade lubricating oils are prepared by addition of viscosity index improvers (IV) Representative examples of agents

  viscosity index improvers are polyalkyl metha-

  crylates, copolymers of ethylene and propylene, copolymers of styrene and a diene, etc. It is also possible to use in the formulations of the invention viscosity index improvers which are at the same time

  times endowed with dispersant properties.

  The lubricating oil used in the

  of the present invention may be a mineral oil or a synthetic oil of proper viscosity

  lubrication and that can be used advantageously-

  in the crankcase of an internal combustion engine.

  Engine lubricating oils usually have a viscosity of about 1300 m 2 2 / s at -17.80 C to 22.7 10-6 m 2 / s at 990 C. The lubricating oils may be from synthetic or natural sources. mineral intended

  to be used as a base oil in the present invention

  vention is chosen between paraffinic oils,

  naphthenic and other oils which are ordinarily

  used in lubricating oil compositions.

  Synthetic oils include both synthetic hydrocarbon oils and synthetic esters.

  Useful synthetic hydrocarbon oils include liquid alpha-olefin polymers having the viscosity

  correct Hydrogenated liquid oligomers of alpha-

  C 6 -C 12 olefins such as 1-decene trimer are particularly useful.

  alkylbenzenes of correct viscosity such as di-

  Dodecylbenzene Useful synthetic esters include esters of monocarboxylic acids and polycarboxylic acids as well as monohydroxyalkanols and polyols. Representative examples include adipate

  of didodecyl, pentaerythritol tetracape

  di-2-ethylhexyl paste, dilauryl sebacate, etc. Complex esters prepared from mixtures of a monocarboxylic acid and the dicarboxylic acid and

  mono and dihydroxyalkanols can also be used.

  ized. Mixtures of hydrocarbon oils with synthetic oils are also useful. For example, mixtures of 10 to 25% by weight of hydrogenated 1-decene trimer with 75 to 90% by weight of a mineral oil.

  Saybolt viscosity at 37.8 C equal to 150 seconds uni-

  versels, give an excellent base for lubricating oil.

fiasco.

  Additive concentrates are also

  included in the scope of the invention.

  typically about 90 to 10% by weight of a screw oil.

  lubricant and about 10 to 90% by weight of the complex additive of the invention. For example, the concentrates contain a sufficient amount of

  diluent to make them easy to handle during the ex-

  puncture and storage Suitable diluents for

  the concentrates include any inert diluent, preferably

  an oil of viscosity suitable for lubrication, so that the concentrate can be easily mixed

  with lubricating oils to prepare the composi-

  Lubricating Oil Advantageous Lubricating Oils

  For example, the use of diluents in the form of diluents includes 38 ° C Saybolt viscosities in the range of from about 35 to about 500 universal seconds, although an oil of lubricating viscosity may be used. Other additives which may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors,

  metal deactivating agents, reducing agents,

  pouring point, anti-oxidants and various

other well-known additives.

  The following examples are presented to illustrate the invention in detail. These examples and illustrations should not be construed as

limiting the scope of the invention.

Example 1

  Preparation of borated glycerol mono-oleate 30.92 g of boric acid and

  250 ml of xylene to a mixture containing 125.23 g mono-

  glycerol oleate (45 to 55% by weight) and glycerol dioleate (55 to 45% by weight) The reaction mixture was heated at 99-141 C for about 9.5 hours under a nitrogen atmosphere under azeotropic conditions We

  collected 17.6 ml of water using a Dean-trap

  Stark The reaction product was filtered and concentrated on a rotary evaporator under vacuum to 135 ° C to obtain 128.35 g of product. Analysis: 2.42 and 2.52% boron, hydroxyl number 32 mg KOH The infrared spectroscopic analysis of the product shows that there is no free hydroxyl extension of the glycerol type but that there is indeed an accentuated BO-H bond and that there is practically no absorption type

BOB.

* Example 2

  The ccane oil mixtures shown in Table I were prepared using 100 N CC oil.

  these mixtures containing 1% by weight of the glyol oleate

  borated cerol prepared in accordance with Example 1, with

  and without the addition of 0.66% w of polyisobutyenyl

  succinimide (prepared by reaction of pplyiso-

  butenylsuccinic whose number average molecular weight of the polyisobutenyl group was about 950 and tetraethylenepentamine in a molar ratio

from amine to anhydride 0.97).

  1 ml of the base oil and each of the mixtures were placed in a 250 ml beaker and placed in a humid chamber maintained at 37.8 C and 90% relative humidity. a disorder and the formation of a sediment in

  samples, as a function of time.

TABLE I

  Formulation Time 0 elapsed, Observation _________ in days Base oil 1-3 light and clear Base oil + 1% in 1 disorder and formation

glycerol oleate weight

  Borated cerol Base oil + 1% by weight Borated glycerol oleate 3

+ 0.66% by weight of poly-

isobuténylsuccinimide

Example 3

  a light and slightly hazy light precipitate A part by weight of the borated glycerol oleate prepared according to Example 1 and 2 parts

  by weight of a solution containing 44% by weight of polyisobutenyl-

  succinimide (prepared by reaction of polyiso-

  butenylsuccinic group whose number average molecular weight of the polyisobutenyl group was about 950 and tetraethylenepentamine in a molar ratio of amine to anhydride of 0.87) in oil (CC 100 N) were were heated together with stirring on a plate

  heating at 170 C for 0.5 hours.

  ml of the reaction mixture was placed in a 250 ml beaker and the beaker was installed

  in a humid chamber maintained at 37.8 C and a humidity

  90% Relative Density A 250 ml beaker containing 1 ml of borated glycerol oleate only, without succinimide, was also placed in the wet chamber

for comparative purposes.

  The borated glycerol oleate hydrolyzed and a film of boric acid formed on its surface after a residence time of about one minute in the wet chamber. The complex formed between borated glycerol oleate and succinimide is remained bright and clear after a week's stay in the humid chamber Even after three weeks, only traces of turbidity were observed in the sample containing

the complex.

Example 4

  Tests have been conducted which demonstrate the fuel economy improvements achieved by adding lubricating oil compositions of the invention to the crankcase of an engine.

motor vehicle.

  In this test, we operated in

  relationship with a dynamometer an Oldsmobile 350 CID engine.

  An engine lubrication system has been designed to allow the correct lubrication of the engine and also to allow the replacement of the oil without

  shut down the engine Basically a system was used

  Dry sump system with external pump for engine lubrication This pump has been connected by valves to four outer casings.

  valve position determined the oil used.

  This test was repeated several times under constant conditions with the base oil and then with the same oil containing 1.25, 1.50 and 2% by weight of the borated glycerol oleate and succinimide complexes prepared according to US Pat. Example 3 Percentages of Improvement in Fuel Consumption Achieved

  using the compositions of the invention,

  base oil, are shown in Table II.

TABLE II

  Fuel economy compared to

basic concentrations of

  tillon Concentration (% by weight) Improvement,%

1.25 1.35

1.5 2.22

2,0 2,62

  Comparisons were made in the test described above with 150 N Exxon-formulated oil additionally containing 30 mmol / kg hydrocarbyl sulfonate.

  overbased magnesium, 2.5% polyisobutenyl

  succinimide at 44% by weight in oil (CC 100 N), 20 mmol / kg of overbased sulfurized calcium polypropylenephénate, 16 mmol / kg of zinc di (alkyl) dithiophosphate, 5.5% of an improving agent the viscosity index based on polyethylene / propylene / diene amine and 3 mmol / kg

  a sulphurized molybdenum-succinimide complex.

  Similarly, engine oils formulated

  each 2% by weight of a succinimide complex

  monoester acid desuif glycerol borate, mono-

  Borated glycerol stearate and borated glycerol monolaurate in place of the borated glycerol oleate complex and succinimide in the above formulations are

  also effective in reducing fuel consumption.

  burner of an internal combustion engine.

  Trials have also indicated that succinimide and borated fatty acid ester complexes

  glycerol of the invention did not exert any

  on the wear of the valve train, such as the wear of the cams and pushers, as determined in the standard IIID test, the wear of the bosses

  of cams, as determined by the standard test method.

  VD sequence, phase 9-L (according to the ASTM acceptance test) and are not corrosive to

copper-lead bearings.

Claims (9)

  1 Composition characterized in that it comprises a complex prepared by reaction of a borated fatty acid ester of glycerol or of mixtures of such esters with a soluble alkyl or alkenylsuccinimide in the oil.   2 Lubricating oil composition, characterized   ridiculous in that it includes a dominant amount of a   viscosity oil suitable for lubrication and a quantity   effective method for reducing friction of a complex prepared by reacting: (a) a borated fatty acid ester of glycerol or mixtures of such esters; and (b) a soluble alkyl or alkenyl succinimide in the oil.   A composition according to claim 1 or 2, characterized in that the borated fatty acid ester of glycerol is a borated glycerol oleate or mixtures of such oleates and said succinimide is a polyisobutenyl succinimide of a polyalkylenepolyamine,   said succinimide being preferably a polyisobutenyl   succinimide of triethylenetetramine or a polyisobutenyl   succinimide of tetraethylenepentamine.   4 Composition according to one of the claims   1 and 2, characterized in that the borated fatty acid ester of glycerol is a mixture containing 45 to 55% by weight of borated glycerol mono-oleate and 55 to 45%   by weight of borated glycerol dioleate, or is the mono- glycerol borate oleate.   Lubricating oil composition according to Claim 2, characterized in that it additionally contains an effective amount of each of the following components: (1) A Group II metal salt of a dihydrocarbyldithiophosphoric acid which is preferably a dialkyldithiophosphate zinc whose alkyl group contains 4 to 12 carbon atoms; (2) a neutral or overbased alkali or alkaline earth metal hydrocarbyl sulfonate or mixtures thereof, said metal being preferably calcium, magnesium or barium or mixtures thereof; (3) a neutralized or overbased alkali or alkaline earth metal alkyl phenate or mixtures of such phenates, said metal being preferably   calcium, magnesium or barium.   Lubricating oil formulation according to claim 5, characterized in that   (1) said dihydrocarbyl acid metal salt   dithiophosphoric acid is O, O-di (2-ethylhexyl) dithio-   zinc phosphate, O, O-di (mixed primary isobutyl / hexyl) zinc dithiophosphate, or O, O-di (sec-butyl / mixed secondary hexyl) zinc dithiophosphate; (2) said metal salt of the sulfonate is a magnesium or calcium overbased hydrocarbyl sulfonate; (3) said metal salt of the phenate is a monoalkyl phenate of calcium or magnesium sulphide overbased rendering.   A method for reducing the fuel consumption of an internal combustion engine, characterized in that it consists in treating its moving surfaces with   a composition according to any one of the claims tions 2 to 6.   8 Lubricating oil concentrate, characterized   in that it comprises 10 to 90% by weight of a lubricating oil   and about 90 to about 10% by weight of a complex prepared by reacting: (a) a borated fatty acid ester of glycerol or a mixture of such esters; and (b) a soluble alkyl or alkenyl succinimide in the oil.   Process for stabilizing a borated fatty acid ester of glycerol against hydrolysis when used in a lubricating oil, characterized in that it comprises reacting said borated fatty acid ester of glycerol with an alkyl or oil-soluble alkenyl succinimide to form a complex which is stable to hydrolysis, said borated fatty acid ester of glycerol being preferably a borated glycerol oleate or mixtures of such esters and said succinimide being   a polyisobutenyl succinimide of a polyalkylenepolyamine.   Process according to claim 9,   in that the succinimide is a polyisobutenyl   succinimide of triethylenetetramine or a polyisobutenyl   succinimide of tetraethylenepentamine, said borated fatty acid ester of glycerol is a mixture containing 45 to 55% by weight of borated glycerol mono-oleate and 55 to 45% by weight of glycerol borate dioleate, or the ester of borated fatty acid glycerol is the mono-oleate of glycerol borate.