Patent Publication Number: US-4224171-A

Title: Novel lubricant additives containing phosphorus and nitrogen and lubricant compositions containing them

Description:
BACKGROUND OF THE INVENTION 
     The present invention relates to novel lubricant additives containing phosphorus and nitrogen and novel lubricant compositions containing them which have improved extreme-pressure and anti-wear properties. 
     A number of additives containing, in particular, phosphorus and nitrogen which make it possible to improve the mechanical properties of lubricating oils are available on the market; among them, mention may be made of the family of the phosphoramidates, such as those described in U.S. Pat. No. 3,810,838. 
     As a result of the present invention, new lubricant compositions have been found of even better performance characteristics. 
     It is, accordingly, an object of the present invention to provide novel lubricants and lubricant additives which provide improved properties. 
     It is a further object of the present invention to provide novel lubricant additives which contain both phosphorus and nitrogen. 
     It is also an object of the present invention to provide novel lubricant compositions which have excellent properties at extreme pressure conditions and which resist wear when used to lubricate metals. 
     Other objects of the invention will be apparent to those skilled in the art from the present disclosure. 
     GENERAL DESCRIPTION OF THE INVENTION 
     The novel lubricant additives which form an object of the invention contain both phosphorus and nitrogen. They comprise a derivative of a compound selected from among the isocyanates and isothiocyanates of formula (I): ##STR1## with a nitrogen-containing compound having at least one ##STR2## radical. In the compound of formula (I), above, Y 1 , Y 2 , X 1  and X 2  are similar or different and represent an oxygen or sulfur atom, and R 1  and R 2  are similar or different and represent a hydrocarbon group. 
     Preferably, R 1  and R 2  are similar or different and represent an alkyl radical of C 3  -C 20 , optionally branched, and preferably C 4  -C 12  ; an alkenyl radical of C 3  -C 24 , optionally branched, and preferably C 3  -C 18  ; a phenyl radical; a phenyl radical substituted by at least one alkyl group of C 1  -C 24  and preferably C 1  -C 12 , or by a cycloalkyl radical of C 3  -C 10  and preferably C 5  -C 8 . 
     In the compound containing at least one ##STR3## radical, the remaining two valences of the nitrogen atom of said nitrogen compound are preferably satisfied by: 
     hydrogen; 
     an alkyl radical of C 1  -C 24 , and preferably C 1  -C 18 , optionally substituted; 
     an alkenyl radical of C 3  -C 24 , and preferably C 3  -C 18  ; 
     an alkynyl radical of C 3  -C 16 , and preferably C 3  -C 8  ; 
     a cycloalkyl radical of C 5  -C 12 , and preferably C 5  -C 9  ; 
     a polycycloalkyl radical of C 9  -C 18  ; 
     a phenyl radical, optionally substituted; 
     a nitrogen heterocyclic radical, optionally substituted, and optionally containing other hetero-elements; 
     organic radicals which form a nitrogen hetero-cycle, optionally substituted, with the said nitrogen atom and contain possibly other hetero-elements. 
     Among the nitrogen-containing compounds corresponding to this preferred type, mention may be made of: 
     ammonia; 
     the primary or secondary alkyl monoamines of C 3  -C 12 , such as butylamine, hexylamine, decylamine, 2-diethylhexylamine, dodecylamine, and dipropylamine; 
     the C 3  -C 12  hydroxymonoamines, such as ethanolamine, propanolamine, diethanolamine, and dipropanolamine; 
     the C 2  -C 12  alkyl diamines, such as hexamethylenediamine and ethylene diamine; 
     the polyamines, such as the polyalkylene amines and tris(3-oxa-6-amino-hexyl)amine; 
     the alkenylsuccinimides derived from the above-mentioned amines and whose alkenyl radical has more than 30 carbon atoms; 
     the alkenylamines derived from the above-mentioned amines and whose alkenyl radical has more than 20 carbon atoms; 
     α-aminopropyl triethoxy silane 
     cyclohexylamine 
     aniline 
     o-aminophenol 
     m-trifluoromethylaniline 
     mercaptotrifluoromethylaniline 
     N(2-butyl-pentyl)N&#39;(phenylene diamine) 
     3-amino-1,2,3-triazole 
     2-amino-benzothiazole 
     2-amino-benzimidazole 
     5-amino-2-mercapto-1,3,4-thiadiazole 
     morpholine 
     Among the isocyanates or isothiocyanates satisfying formula (I), included are the products of the following formulae: ##STR4## 
     The derivatives of phosphorus and nitrogen which enter into the compositions forming the object of the invention are prepared by the action of an isocyanate or isothiocyanate of formula (I), above, on a nitrogen-containing compound as defined above, in accordance with a ratio of the number of isocyanate or isothiocyanate groups to the number of active ##STR5## of between about 0.5 and 1.25. 
     The reaction is desirably carried out at a temperature of between about 20° C. and 100° C., and preferably between about 20° C. and 70° C., for about one-half hour to 10 hours, and preferably for between about 3/4 hour to 8 hours. 
     The reaction may optionally be carried out in the presence of an aliphatic solvent (pentane, hexane, etc.) or a benzene solvent (benzene, toluene, etc.), possibly mixed with a polar aprotic solvent (hexamethylphosphorotriamide, N-methyl-pyrolidone, dimethylformamide, dimethylsulfoxide, etc.). 
     The reaction product is then washed, dried and finally purified. 
     The lubricating oils to which the lubricant additives of the invention may be added include natural oils of a viscosity of between 20.6 cst (centistokes) and 541 cst at 37.8° C., namely, between 100 and 2500 SUS (Saybolt Universal Viscosity) at 100° F., or synthetic or semi-synthetic bases (synthetic hydrocarbons, esters, polyesters, polyethers) of comparable viscosities. 
     The quantities of phosphorus and nitrogen containing lubricant additives which can be introduced into the lubricant compositions forming an object of the invention are between about 0.2 and 10 percent by weight of said composition. The particular quantity of additives is a function of the future use of the compositions, namely, as motor, gear-box, or automatic transmission oils, hydraulic fluid, or cutting oil for the mechanical industry. 
     The compositions which form the object of the invention may also contain anti-oxidant, anti-corrosion, anti-foam, detergent dispersion additives, other extreme-pressure and anti-wear adjuvants, etc., without there resulting herefrom any problem with respect to compatibility or loss in level of performance. 
     The lubricant compositions which form the object of the invention may be prepared by dissolving the lubricant additive of the invention in the base oil or, when other adjuvants are to be present, by dissolving the additive in the base oil to which said adjuvants have been added or by dissolving the additive in the said adjuvants and adding the base oil. 
    
    
     SPECIFIC DESCRIPTION OF THE INVENTION 
     In order to disclose more clearly the nature of the present invention, the following examples illustrating the invention are given. It should be understood, however, that this is done solely by way of example and is intended neither to delineate the scope of the invention nor limit the ambit of the appended claims. In the examples which follow, and throughout the specification, the quantities of material are expressed in terms of parts by weight, unless otherwise specified. 
     EXAMPLE 1 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(hexyl)thiourea of the formula ##STR6## 
     Into a 250 ml. three-necked, round-bottom flask there are introduced 48.5 g. (namely, 0.15 mol) of O,O-dihexylisothiocyanothiophosphate, whereupon 17 g. (i.e., 0.165 mol) of hexylamine are added dropwise over the course of 30 minutes. The temperature is maintained at 24°-25° C. for 45 minutes. A colored homogeneous medium is obtained. 
     60 ml. of pentane are then added to the medium. The aqueous solution obtained is washed with 50 ml. of distilled water, decanted, and then dried over sodium sulfate. 
     After distillation of the pentane under vacuum to remove it, there are obtained 58 g. of product, an oil, having the following composition, determined by elementary analysis: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.0           7.31                                            
sulfur      12.9          15.09                                           
nitrogen    6.3           6.60                                            
carbon      54.5          53.77                                           
hydrogen    10            9.67                                            
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     The conversion rate with respect to the O,O-dihexylisothiocyanothiophosphate used is 79%. 
     The yield with respect to the starting material which has reacted is 87%. 
     The O,O-dihexylisothiocyanothiophosphate used may be prepared in the following manner: 
     Into a 3 liter three-necked, round-bottom flask there are introduced, with agitation, 361 g. (namely, 3.72 mols) of potassium thiocyanate and 1 liter of dry acetone, whereupon 1015 g. (namely, 3.38 mols) of O,O-dihexylchlorothiophosphate are introduced over the course of 3 hours and 40 minutes, maintaining the temperature at 25°-30° C., a precipitate of KCl is formed. 
     At the end of the introduction, heating is effected under acetone reflux for two hours. The reaction mixture is allowed to cool, whereupon the acetone solution is decanted and the precipitate which remains is washed with 500 ml. of dry acetone. 
     The acetone solutions are combined and then distilled under vacuum. In this way there are recovered 771 g. of O,O-dihexylisothiocyanothiophosphate, which is confirmed by elementary analysis: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  8.9           9.60                                            
sulfur      18.2          19.81                                           
nitrogen    4.0           4.33                                            
______________________________________                                    
 
    
     EXAMPLE 2 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula ##STR7## 
     The procedure described in Example 1 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 10 g. (namely, 0.1 mol) of dipropylamine. 
     There are obtained 40 g. of an oil having the following composition, as determined by elementary analysis: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.3           7.31                                            
nitrogen    6.2           6.60                                            
sulfur      14.9          15.09                                           
carbon      55.3          53.8                                            
hydrogen    9.9           9.67                                            
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     The conversion rate is 89%. 
     The yield is 98%. 
     EXAMPLE 3 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(decyl)thiourea of the formula ##STR8## 
     The procedure described in Example 1 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 17.5 g. (namely, 0.1 mol) of decylamine. 
     There are obtained 47 g. of product the composition of which, determined by elementary analysis is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.1           6.46                                            
nitrogen    5.8           5.83                                            
sulfur      11.3          13.33                                           
carbon      59.0          57.50                                           
hydrogen    10.5          10.21                                           
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     The conversion rate is 87.7%. 
     The yield is 100%. 
     EXAMPLE 4 
     Preparation of N(O,O-dihexlphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(dodecyl)thiourea of the formula: ##STR9## 
     The procedure described in Example 1 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 20.5 g. (namely, 0.11 mol) of dodecylamine solubilized in 70 ml. of pentane. 
     There are obtained 50 g. of an oil having the composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  5.6           6.10                                            
sulfur      10.5          12.60                                           
carbon      59.8          59.05                                           
hydrogen    10.60         10.43                                           
nitrogen    5.20          5.51                                            
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     The conversion rate is 90.2%. 
     The yield is 100%. 
     EXAMPLE 5 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(cyclohexyl)thiourea of the formula ##STR10## 
     The procedure described in Example 1 is repeated but employing the following reactants: 48.5 g. (namely, 0.15 mol) of O,O-dihexylisothiocyanothiophosphate and 16.5 g. (namely, 0.165 mol) of cyclohexylamine. 
     There are obtained 62 g. of an oil having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7             7.35                                            
sulfur      13.2          15.7                                            
carbon      54.0          54.03                                           
hydrogen    9.4           9.24                                            
nitrogen    7.1           6.64                                            
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     The conversion rate is 92.3%. 
     The yield is 91.3%. 
     EXAMPLE 6 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(phenyl)thiourea of the formula ##STR11## 
     The procedure described in Example 1 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 10.5 g. (namely, 0.11 mol) of aniline. 
     The product obtained is taken up in 50 ml. of pentane. After washing and distillation of the solvent, there are obtained 41 g. of an oil having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.6           7.45                                            
sulfur      13.1          15.38                                           
nitrogen    6.5           6.73                                            
carbon      55.5          54.81                                           
hydrogen    8.0           7.93                                            
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     The conversion rate is 71.3%. 
     The yield is 45%. 
     EXAMPLE 7 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(o-hydroxyphenyl)thiourea of the formula ##STR12## 
     There are introduced into a 250 ml., three-necked, round-bottom flask 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate, 12 g. (namely, 0.11 mol) of o-aminophenol and 50 ml. of toluene. 5 ml. of hexamethylphosphotriamide are added and heating is effected for 21/2 hours at 50° C. Once cooled, the medium is washed with 50 ml. of water and then decanted. The solvent is distilled under vacuum. 
     There are obtained 42 g. of an oil having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.8           7.18                                            
sulfur      12.2          14.81                                           
nitrogen    6.7           6.48                                            
carbon      53.2          52.78                                           
hydrogen    7.6           7.64                                            
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     The conversion rate is 82%. 
     The yield is 45.5%. 
     EXAMPLE 8 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(butyl)thiourea of the formula ##STR13## 
     The procedure described in Example 1 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 8 g. (namely, 0.11 mol) of butylamine. The temperature is maintained at 30° C. for 1 hour. Then the product is taken up in 50 ml. of pentane. 
     There are obtained 38 g. of an oil having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.3           7.83                                            
carbon      50.5          51.51                                           
hydrogen    9.2           9.34                                            
sulfur      15.0          16.16                                           
nitrogen    6.7           7.07                                            
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     The conversion rate is 81%. 
     The yield is 100%. 
     EXAMPLE 9 
     Preparation of N(O,O-dihexylphosphorothiono-N(hydrogen)-N&#39;(hydrogen)-N&#39;(2-ethyl hexyl)thiourea of the formula ##STR14## 
     The procedure described in Example 8 is repeated but employing as reactants 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate and 14.2 g. (namely, 0.11 mol) of 2-ethyl hexylamine. 
     There are obtained 44 g. of a viscous product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.5           6.86                                            
carbon      54.5          55.75                                           
hydrogen    9.8           9.95                                            
nitrogen    5.8           6.19                                            
sulfur      13.2          14.16                                           
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     The conversion rate is 85%. 
     The yield is 100%. 
     EXAMPLE 10 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(1,2,3-triazyl-5)thiourea of the formula ##STR15## 
     48.5 g. (namely, 0.15 mol) of O,O-dihexylisothiocyanothiophosphate, 14 g. of 3-amino-1,2,3-triazol and 30 ml. of pentane are introduced into a 250 ml. round-bottom flask. This mixture is heated at 50° C. whereupon 30 ml. of hexamethylphosphotriamide are added. The operation requires 71/2 hours. After cooling, the mixture is washed with two portions of 60 ml. of water, then decanted and the solvent is eliminated by vacuum distillation. 
     There are obtained 59 g. of product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  8.6           7.62                                            
carbon      44.6          44.23                                           
hydrogen    7.9           7.37                                            
sulfur      13.6          15.72                                           
nitrogen    13.7          17.20                                           
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     The conversion rate is 73%. 
     The yield is 100%. 
     EXAMPLE 11 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(2-benzothiazyl)thiourea of the formula ##STR16## 
     The operation described in Example 13 is repeated but employing as reactants 39 g. (namely, 0.12 mol) of O,O-dihexylisothiocyanothiophosphate, 20 g. (namely, 0.132 mol) of 2-amino benzothiazole, and 50 ml. of hexamethylphosphotriamide, in 100 ml. of toluene. The reaction proceeds for 21/2 hours at a temperature of 50° C. 
     There are obtained 58 g. of a product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
carbon      50.5          50.74                                           
hydrogen    7.0           6.77                                            
sulfur      19.7          20.30                                           
phosphorus  7.0           6.55                                            
nitrogen    9             8.88                                            
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     The conversion rate is 80.7%. 
     The yield is 91.4%. 
     EXAMPLE 12 
     Preparation of N(O,O-dihexylphosphorothiono-N(hydrogen)-N&#39;(1,3,4-mercaptothiadiazole)thiourea of the formula ##STR17## 
     The procedure described in Example 10 is repeated with 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate, 14.6 g. (namely, 0.11 mol) of 5-amino 2-mercapto-1,3,4-thiadiazole, 50 ml. of toluene and 50 ml. of hexamethylphosphotriamide for 11/2 hours at 65° C. 
     There are obtained 44 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.40          6.8                                             
nitrogen    11.7          12.28                                           
sulfur      26.8          28.07                                           
carbon      40.2          39.47                                           
hydrogen    6.5           6.36                                            
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     The conversion rate is 7.8%. 
     The yield is 91.2%. 
     EXAMPLE 13 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(benzimidazolyl)thiourea of the formula ##STR18## 
     The procedure described in Example 10 is repeated but employing 32.3 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanothiophosphate, 14.6 g. (namely, 0.11 mol) of 2-amino benzimidazole, 50 ml. of toluene and 50 ml. of hexamethylphosphorotriamide for 3 hours at 50° C. 
     There are obtained 47 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.1           6.80                                            
nitrogen    11.8          12.28                                           
sulfur      13.7          14.04                                           
carbon      52.0          52.63                                           
hydrogen    7.1           7.24                                            
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     The conversion rate is 38%. 
     The yield is 77%. 
     EXAMPLE 14 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(morpholinyl)thiourea of the formula ##STR19## 
     The procedure described in Example 10 is repeated but employing 32.3 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanothiophosphate, 9.6 g. (namely, 0.11 mol) of morpholine, 50 ml. of toluene and 50 ml. of hexamethylphosphorotriamide for 3 hours at 50° C. 
     There are obtained 38 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  8.0           7.56                                            
nitrogen    6.5           6.83                                            
sulfur      15.2          15.61                                           
carbon      49.5          49.76                                           
hydrogen    8.4           8.54                                            
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     The conversion rate is 45%. 
     The yield is 80%. 
     EXAMPLE 15 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(3-trifluoromethyl phenyl)thiourea of the formula ##STR20## 
     The procedure described in Example 1 is repeated but employing 32.3 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanothiophosphate, 16.25 g. (0.11 mol) of m-trifluoromethylaniline, and 60 ml. of pentane for 1 hour at 28° C. 
     There are obtained 47 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.1           6.40                                            
sulfur      12.7          13.22                                           
nitrogen    5.1           5.79                                            
carbon      50.2          49.59                                           
hydrogen    6.9           6.61                                            
fluorine    10.9          11.78                                           
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     The conversion rate is 75%. 
     The yield is 72%. 
     EXAMPLE 16 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(mercaptotrifluoromethylphenyl)thiourea of the formula ##STR21## 
     The procedure described in Example 1 is repeated but employing 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate, 21.2 g. (namely, 0.11 mol) of mercaptotrifluoromethylaniline, and 60 ml. of pentane, for 2 hours at 35° C. 
     There are obtained 46 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  5.8           6.00                                            
sulfur      17.9          18.60                                           
nitrogen    5.0           5.43                                            
carbon      46.6          46.51                                           
hydrogen    6.3           6.20                                            
fluorine    10.8          11.05                                           
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     EXAMPLE 17 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(triethoxysilylpropyl)thiourea of the formula ##STR22## 
     The procedure described in Example 1 is repeated but employing 32.3 g. (namely, 0.1 mol) of O,O-dihexylisothiocyanothiophosphate, 24.2 g. (namely, 0.11 mol) of γ aminopropyltriethoxysilane, and 50 ml. of toluene, for 11/2 hours at 35° C. 
     There are obtained 48 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  5.6           5.70                                            
sulfur      11.5          11.76                                           
nitrogen    4.8           5.14                                            
carbon      49.3          48.53                                           
hydrogen    9.3           9.01                                            
silicon     4.90          5.15                                            
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     The conversion rate is 100%. 
     The yield is 100%. 
     EXAMPLE 18 
     Preparation of tris[[3(O,O-dihexylphosphorothiono)ureido] 6  3-oxa hexyl]amine, of the formula ##STR23## 
     The procedure described in Example 1 is repeated but employing 48 g. (namely, 0.15 mol) of O,O-dihexylisothiocyanothiophosphate, 17.6 g. (namely, 0.055 mol) of tris(6-amino-3-oxa-hexyl)amine, and 70 ml. of toluene, for 2 hours at 50° C. 
     There are obtained 59 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.8           7.21                                            
sulfur      13.7          14.9                                            
nitrogen    6.9           7.60                                            
carbon      51.3          50.27                                           
hydrogen    8.9           8.84                                            
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     The conversion rate is 100%. 
     The yield is 100%. 
     EXAMPLE 19 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(p-phenylanilinophenyl)-N&#39;(butyl-2-n-pentyl)thiourea of the formula ##STR24## 
     The procedure described in Example 1 is repeated but employing 32.3 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanothiophosphate, 34 g. (namely, 0.11 mol) of N(butyl-2-n-pentyl)N&#39;-phenylene diamine, and 60 ml. of toluene, for 21/2 hours at 45° C. 
     There are obtained 60 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  4.1           4.90                                            
sulfur      9.6           10.11                                           
nitrogen    7.1           6.64                                            
carbon      65.3          64.45                                           
hydrogen    8.7           8.85                                            
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     The conversion rate is 100%. 
     The yield is 100%. 
     EXAMPLE 20 
     Preparation of bis[N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(hydrogen)thiourea]hexylene of the formula ##STR25## 
     The procedure described in Example 1 is repeated but employing 51.6 g. (namely, 0.16 mol) of O,O-dihexylisothiocyanothiophosphate, 10.2 g. (namely, 0.088 mol) of hexamethylene diamine, and 40 ml. of toluene, for 1 hour at 27° C. 
     There are obtained 56 g. of product having a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.7           8.14                                            
sulfur      16.1          16.80                                           
nitrogen    6.9           7.35                                            
carbon      51.0          50.39                                           
hydrogen    8.9           8.92                                            
______________________________________                                    
 
    
     The conversion rate is 98%. 
     The yield is 86%. 
     EXAMPLE 21 
     Preparation of mixtures of tris(O,O-dihexylphosphorothionothiocarbamyl)-1-(polyisobutenylsuccinimido)3,6,9,12-tetraza dodecanes 
     Into a 250 ml. three-necked, round-bottom flask there are introduced 24.5 g. (0.076 mol) of O,O-dihexylisothiocyanothiophosphate and 84.5 g. (namely, 0.076 gram atoms of active nitrogen) of a monopolyisobutenylsuccinimide containing 3.10% nitrogen, including 1.26% active nitrogen, coming from the reaction of tetraethylene pentamine and a polyisobutenylsuccinic anhydride of an acid number equal to 74 obtained by condensation of maleic anhydride on a polyisobutene of a number average molecular weight of 1000. The mixture is heated for 21/2 hours at 50° C. There are obtained 87 g. of a product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
                   Value                                                  
                   Found (%)                                              
______________________________________                                    
phosphorus           2.21                                                 
sulfur               4.48                                                 
total nitrogen       2.46                                                 
______________________________________                                    
 
    
     EXAMPLE 22 
     Preparation of bis 3-6(O,O-dihexylphosphorothionothiocarbamyl)bis-1-8(polyisobutylsuccinimido)-3-6-diazo octane 
     Into a 250 ml. three-necked, round-bottom flask there are introduced 7 g. (namely, 0.0217 mol) of O,O-dihexylisothiocyanothiophosphate and 55 g. (namely, 0.0217 gram atoms of active nitrogen) of a bis-polyisobutenylsuccinimide containing 1.2% nitrogen including 0.6% active nitrogen, obtained from the reaction of triethylene tetramine and a polyisobutenyl succinic anhydride of an acid number equal to 74, obtained by condensation of maleic anhydride on a polyisobutene of number average molecular weight of 1000. The mixture is heated for 21/2 hours at 45° C. 
     There are obtained 62 g. of product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
                   Value                                                  
                   Found (%)                                              
______________________________________                                    
phosphorus           1.12                                                 
sulfur               2.50                                                 
nitrogen             1.82                                                 
______________________________________                                    
 
    
     EXAMPLE 23 
     Preparation of N(O,O-dihexylphosphoro)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula: ##STR26## 
     By a procedure equivalent to that described in Example 1, 15.35 g. (namely, 0.05 mol) of O,O-dihexylisothiocyanophosphate, and 5.05 g. (namely, 0.05 mol) of dipropylamine are contacted for 4 hours at room temperature. 
     There are obtained 21 g. of product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.4           7.60                                            
sulfur      7.2           7.84                                            
nitrogen    6.1           6.86                                            
carbon      55.2          55.88                                           
hydrogen    9.8           10.05                                           
______________________________________                                    
 
    
     The conversion rate is 92%. 
     The yield is 100%. 
     The O,O-dihexylisothiocyanophosphate can be obtained under conditions equivalent to those described in Example 1 so as to obtain O,O-dihexylisothiocyanothiophosphate from potassium thiocyanate and O,O-dihexylchlorophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  9.8           10.10                                           
sulfur      10            10.42                                           
nitrogen    4.10          4.56                                            
carbon      50.60         50.81                                           
hydrogen    8.35          8.47                                            
______________________________________                                    
 
    
     EXAMPLE 24 
     Preparation of N(O,O-dihexylphosphoro)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(dodecyl)thiourea of the formula ##STR27## 
     In accordance with a procedure equivalent to that described in Example 4, above, 30.7 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanophosphate and 20.5 g. (namely, 0.11 mol) of n-dodecylamine are contacted. 
     There are obtained 47 g. of product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.15          6.3                                             
sulfur      5.3           6.5                                             
nitrogen    5.3           5.69                                            
carbon      59.9          60.98                                           
hydrogen    10.5          10.77                                           
______________________________________                                    
 
    
     The conversion rate is 93.5%. 
     The yield is 98%. 
     EXAMPLE 25 
     Preparation of N(O,O-dihexylphosphoro)-N(hydrogen)-N&#39;(hydrogen)-N&#39;(triethoxysilylpropyl)thiourea of the formula ##STR28## 
     In accordance with a method of operation equivalent to that described in Example 16, above, 30.7 g. (namely, 0.10 mol) of O,O-dihexylisothiocyanophosphate and 24.2 g. (namely, 0.11 mol) of γaminopropyltriethoxysilane are contacted. 
     There are obtained 52 g. of product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  5.7           5.87                                            
sulfur      5.85          6.06                                            
nitrogen    5.1           5.30                                            
carbon      49.7          50.0                                            
hydrogen    9.1           9.28                                            
silicon     5.2           5.30                                            
______________________________________                                    
 
    
     The conversion rate is 86%. 
     The yield is 92.5%. 
     EXAMPLE 26 
     Preparation of N(S,S-dihexylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula ##STR29## 
     In accordance with a procedure equivalent to that described in Example 1, above, 35.5 g. (0.1 mol) of S,S-dihexylisothiocyanothiophosphate and 10 g. (0.1 mol) of dipropylamine are contacted for 3/4 hour at 25° C. 
     There are obtained 41 g. of product of a component, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  6.7           6.8                                             
sulfur      27.5          28.07                                           
nitrogen    5.9           6.14                                            
carbon      49.8          50.0                                            
hydrogen    8.75          8.99                                            
______________________________________                                    
 
    
     The conversion rate is 79%. 
     The yield is 84%. 
     The S,S-dihexylisothiocyanothiophosphate used can be obtained under conditions equivalent to those described in Example 1 so as to obtain the O,O-dihexylisothiocyanothiophosphate from potassium thiocyanate and S,S-dihexylchlorothiophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  8.5           8.73                                            
sulfur      35.5          36.06                                           
nitrogen    3.7           3.94                                            
carbon      43.7          43.94                                           
hydrogen    7.2           7.32                                            
______________________________________                                    
 
    
     EXAMPLE 27 
     Preparation of N(O,O-diallylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula ##STR30## 
     In accordance with a procedure equivalent to that described in Example 1, above, 23.5 g. (0.1 mol) of O,O-diallylisothiocyanothiophosphate and 10 g. (0.1 mol) of dipropylamine are contacted. 
     There are obtained 30 g. of a product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  9.1           9.23                                            
sulfur      18.7          19.05                                           
nitrogen    8.1           8.33                                            
carbon      46.6          46.43                                           
hydrogen    7.5           7.44                                            
______________________________________                                    
 
    
     The conversion rate is 94%. 
     The yield is 97%. 
     The O,O-diallylisothiocyanothiophosphate can be obtained under conditions equivalent to those described in Example 1 in order to obtain the O,O-dihexylisothiocyanothiophosphate from potassium thiocyanate and O,O-diallylchlorothiophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  13.0          13.19                                           
sulfur      26.9          27.23                                           
nitrogen    5.7           5.96                                            
carbon      35.7          35.74                                           
hydrogen    4.3           4.26                                            
______________________________________                                    
 
    
     EXAMPLE 28 
     Preparation of N(O,O-dibutylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula ##STR31## 
     In accordance with a procedure equivalent to that described in Example 1, above, 26.5 g. (0.1 mol) of O,O-dibutylisothiocyanothiophosphate and 10 g. (0.1 mol) of dipropylamine are contacted. 
     There are obtained 34 g. of a product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  8.3           8.42                                            
sulfur      17.1          17.39                                           
nitrogen    7.4           7.61                                            
carbon      49.1          48.91                                           
hydrogen    9.2           8.97                                            
______________________________________                                    
 
    
     The conversion rate is 92%. 
     The yield is 100%. 
     The O,O-dibutylisothiocyanothiophosphate used can be obtained under conditions equivalent to those described in Example 1 in order to obtain the O,O-dibutylisothiocyanothiophosphate from potassim thiocyanate and O,O-dibutylchlorophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  11.4          11.61                                           
sulfur      23.7          23.97                                           
nitrogen    5.0           5.24                                            
carbon      40.6          40.45                                           
hydrogen    6.8           6.74                                            
______________________________________                                    
 
    
     EXAMPLE 29 
     Preparation of N(O,O-dinonylphenylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)thiourea of the formula ##STR32## 
     In accordance with a procedure equivalent to that described in Example 1, above, 10.0 g. (0.1 mol) of dipropylamine and 55.9 g. (0.1 mol) of O,O-dinonylphenylisothiocyanothiophosphate are contacted. 
     There are obtained 62 g. of a product of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  4.5           4.70                                            
sulfur      9.4           9.70                                            
nitrogen    4.0           4.24                                            
carbon      67.6          67.27                                           
hydrogen    9.4           9.24                                            
______________________________________                                    
 
    
     The conversion rate is 90%. 
     The yield is 98%. 
     The O,O-dinonylphenylthiocyanothiophosphate used can be obtained under conditions equivalent to those described in Example 1 in order to obtain the O,O-dihexylisothiocyanothiophosphate from potassium thiocyanate and the O,O-dinonylphenylchlorothiophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  5.4           5.55                                            
sulfur      11.3          11.45                                           
nitrogen    2.4           2.50                                            
carbon      66.2          66.55                                           
hydrogen    8.3           8.23                                            
______________________________________                                    
 
    
     EXAMPLE 30 
     Preparation of N(O,O-dihexylphosphorothiono)-N(hydrogen)-N&#39;(dipropyl)urea of the formula ##STR33## 
     In accordance with a procedure equivalent to that described in Example 1, above, 30.7 g. (0.1 mol) of O,O-dihexylisocyanothiophosphate and 10 g. (0.1 mol) of dipropylamine are contacted. 
     There are obtained 38 g. of an oil of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.5           7.6                                             
nitrogen    6.7           6.86                                            
sulfur      7.6           7.84                                            
carbon      55.7          55.88                                           
hydrogen    9.9           10.05                                           
______________________________________                                    
 
    
     The conversion rate is 95%. 
     The yield is 98%. 
     The O,O-dihexylisocyanothiophosphate used can be obtained under conditions equivalent to those described in Example 1 from potassium isocyanate and O,O-dihexylchlorothiophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  10.0          10.10                                           
nitrogen    4.4           4.56                                            
sulfur      10.2          10.42                                           
carbon      50.3          50.83                                           
hydrogen    8.4           8.47                                            
______________________________________                                    
 
    
     EXAMPLE 31 
     Preparation of N(O,O-dihexylphosphoro)-N(hydrogen)-N&#39;(dipropyl)urea of the formula ##STR34## 
     In accordance with a procedure equivalent to that described in Example 1, above, 29.1 g. (0.1 mol) of O,O-dihexylisocyanophosphate and 10 g. (0.1 mol) of dipropylamine are contacted. 
     There are obtained 37 g. of an oil of a composition, determined by elementary analysis, of: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  7.8           7.91                                            
nitrogen    7.0           7.14                                            
carbon      58.0          58.16                                           
hydrogen    10.4          10.46                                           
______________________________________                                    
 
    
     The conversion rate is 94%. 
     The yield is 96%. 
     The O,O-dihexylisocyanophosphate used can be obtained under conditions similar to those described in Example 23 from potassium isocyanate and O,O-dihexylchlorophosphate. The composition of the product obtained, determined by elementary analysis, is: 
     
         ______________________________________                                    
          Value       Value                                               
          Found (%)   Calculated (%)                                      
______________________________________                                    
phosphorus  10.4          10.65                                           
nitrogen    4.6           4.82                                            
carbon      53.4          53.61                                           
hydrogen    8.8           8.93                                            
______________________________________                                    
 
    
     EXAMPLE 32 
     A lubricant composition is prepared by adding to a 10W30 oil an amount of product obtained from one of Examples 1 to 31, corresponding to 0.9% phosphorus by weight. 
     The mechanical properties of these resulting lubricant compositions are tested on: 
     (1) Four-ball machine, in accordance with ASTM Standard D 2783-69 T. This test gives the diameter in millimeters of the imprint under a seizing load of 70, 90, 110 and 130 kg., as well as the welding load in kilograms. 
     (2) Falex machine--this test indicates the wear of the pin (that is to say, of the wear specimen) in mg. at the end of 30 minutes under a pressure of 500 lbs. (271.5 kg.). 
     The resistance to oxidation of this composition is evaluated by the Mobil oxidation test consisting of oxidizing 33 g. of oil containing the additive, heating to 180° C. for 48 hours in the presence of oxidation catalysts (Pb-Cu) in a flow of air of 13.9 liters per hour, and measuring the increase in viscosity at 210° F. (98.9° C.) of the oxidized oil as compared with new oil. 
     Comparable tests were carried out on compositions in which the product of one of Examples 1 to 31 is replaced by the same quantity, expressed in % of phosphorus, and one of the following commmercial additives, all containing phosphorus and nitrogen, with the exception of additive G: 
     additive A: &#34;TLA 202&#34; marketed by Texaco Inc. 
     additive B: &#34;Improvex 33&#34; marketed by Rhone-Poulenc 
     additive C: &#34;Ortholeum 535&#34; marketed by Du Pont de Nemours 
     additive D: &#34;Eca 5215&#34; marketed by Oronite 
     additive E: &#34;Oloa 259&#34; marketed by Exxon 
     additive F: &#34;Lubrizol 797&#34; marketed by Lubrizol 
     additive G: base of a mixture of zinc alkyldithiophosphate, the alkyl radicals of which contain 4 to 6 carbon atoms. 
     The results of all of these tests are given in Tables 1, 1a, 1b and 1c, respectively, appearing below. 
     
                                           TABLE 1                                 
__________________________________________________________________________
          Mechanical Properties                                           
                               After                                      
          Before Oxidation     Oxidation                                  
                                      Oxidation                           
     % by Four-Ball Test       Seizure                                    
                                      Increase                            
Products                                                                  
     Weight                                                               
          Seizure imprint in mm.                                          
                      Welding                                             
                           Falex                                          
                               imprint                                    
                                      in                                  
of   of   70 90 110                                                       
                   130                                                    
                      load in  in     Viscosity                           
Examples                                                                  
     Product                                                              
          kg.                                                             
             kg.                                                          
                kg.                                                       
                   kg.                                                    
                      kg.  mm. mm.-100 kg.                                
                                      %                                   
__________________________________________________________________________
1    1.42 -- 0.43                                                         
                0.50                                                      
                   0.91                                                   
                      300  1.9 1.9    40                                  
2    1.37 -- 0.48                                                         
                0.49                                                      
                   0.90                                                   
                      250  3.3 2.0    30                                  
3    1.64 -- 0.46                                                         
                1.90                                                      
                   -- 250  5.2 1.4    40                                  
4    1.79 -- 0.42                                                         
                1.70                                                      
                   -- 250  3.0 1.7    20                                  
5    1.43 -- 0.48                                                         
                0.50                                                      
                   2.5                                                    
                      300  2.4 1.8    20                                  
6    1.52 -- 0.47                                                         
                0.50                                                      
                   2.0                                                    
                      300  6.0 1.8    30                                  
7    1.47 -- 0.47                                                         
                0.52                                                      
                   2.5                                                    
                      300  4.0 1.9    30                                  
8    1.37 -- 0.46                                                         
                0.53                                                      
                   0.95                                                   
                      300  1.8 1.7    30                                  
9    1.54 -- 0.42                                                         
                1.50                                                      
                   -- 250  3.0 1.9    40                                  
10   1.16 -- 0.44                                                         
                1.80                                                      
                   -- 250  3.4 1.6    30                                  
__________________________________________________________________________
 
    
     
                                           TABLE 1a                                
__________________________________________________________________________
          Mechanical Properties                                           
                               After                                      
                               Oxidation                                  
                                      Oxidation                           
% by      Before Oxidation     Seizure                                    
                                      Increase                            
Products                                                                  
     Weight                                                               
          Seizure imprint in mm.                                          
                      Welding                                             
                           Falex                                          
                               imprint                                    
                                      in                                  
of   of   70 90 110                                                       
                   130                                                    
                      load in  in     Viscosity                           
Examples                                                                  
     Product                                                              
          kg.                                                             
             kg.                                                          
                kg.                                                       
                   kg.                                                    
                      kg.  mm. mm.-100 kg.                                
                                      %                                   
__________________________________________________________________________
11   1.43 -- 0.45                                                         
                1.90                                                      
                   -- 250  2.9 2.0    150                                 
12   1.35 -- 0.44                                                         
                0.60                                                      
                   2.5                                                    
                      300  0.8 1.6    50                                  
13   1.41 -- 0.46                                                         
                1.40                                                      
                   -- 250  4.1 2.0    150                                 
14   1.25 -- 0.48                                                         
                1.45                                                      
                   -- 250  3.8 2.0    120                                 
15   1.64 -- 0.44                                                         
                0.48                                                      
                   0.92                                                   
                      300  3.6 1.7    20                                  
16   1.72 -- 0.45                                                         
                0.49                                                      
                   0.91                                                   
                      300  3.4 1.8    30                                  
17   1.79 -- 0.40                                                         
                0.52                                                      
                   2.0                                                    
                      300  3.4 1.7    30                                  
18   1.47 -- 0.43                                                         
                0.51                                                      
                   1.5                                                    
                      300  3.7 1.4    60                                  
19   2.44 -- 0.49                                                         
                0.43                                                      
                   2.5                                                    
                      300  3.6 1.6    20                                  
20   1.30 -- 0.50                                                         
                0.90                                                      
                   -- 300  3.7 1.9    20                                  
__________________________________________________________________________
 
    
     
                                           TABLE 1b                                
__________________________________________________________________________
          Mechanical Properties                                           
                               After                                      
                               Oxidation                                  
                                      Oxidation                           
% by      Before Oxidation     Seizure                                    
                                      Increase                            
Products                                                                  
     Weight                                                               
          Seizure imprint in mm.                                          
                      Welding                                             
                           Falex                                          
                               imprint                                    
                                      in                                  
of   of   70 90 110                                                       
                   130                                                    
                      load in  in     Viscosity                           
Examples                                                                  
     Product                                                              
          kg.                                                             
             kg.                                                          
                kg.                                                       
                   kg.                                                    
                      kg.  mm. mm.-100 kg.                                
                                      %                                   
__________________________________________________________________________
21   4.52 -- 0.45                                                         
                1.50                                                      
                   -- 250  6.5 2.0    150                                 
22   8.93 -- 0.47                                                         
                1.80                                                      
                   -- 250  4.1 2.0    150                                 
23   1.35 -- 0.43                                                         
                0.49                                                      
                   0.93                                                   
                      300  3.4 1.6    70                                  
24   1.63 -- 0.47                                                         
                1.80                                                      
                   -- 250  3.5 2.0    50                                  
25   1.75 -- 0.42                                                         
                0.53                                                      
                   2.5                                                    
                      300  3.1 1.8    100                                 
26   1.49 -- 0.40                                                         
                0.51                                                      
                   0.92                                                   
                      300  3.2 1.7    30                                  
27   1.10 -- 0.49                                                         
                0.55                                                      
                   2.4                                                    
                      250  3.8 2.0    100                                 
28   1.20 -- 0.43                                                         
                0.48                                                      
                   0.90                                                   
                      300  3.0 1.8    30                                  
29   2.22 -- 0.45                                                         
                0.53                                                      
                   0.97                                                   
                      250  3.2 1.9    50                                  
30   1.33 -- 0.47                                                         
                0.50                                                      
                   2.5                                                    
                      250  3.2 1.9    30                                  
31   1.28 -- 0.46                                                         
                0.52                                                      
                   -- 250  3.5 2.0    80                                  
__________________________________________________________________________
 
    
     
                                           TABLE 1c                                
__________________________________________________________________________
          Mechanical Properties                                           
                               After                                      
                               Oxidation                                  
                                      Oxidation                           
% by      Before Oxidation     Seizure                                    
                                      Increase                            
Products                                                                  
     Weight                                                               
          Seizure imprint in mm.                                          
                      Welding                                             
                           Falex                                          
                               imprint                                    
                                      in                                  
of   of   70 90 110                                                       
                   130                                                    
                      load in  in     Viscosity                           
Examples                                                                  
     Product                                                              
          kg.                                                             
             kg.                                                          
                kg.                                                       
                   kg.                                                    
                      kg.  mm. mm.-100 kg.                                
                                      %                                   
__________________________________________________________________________
A    10   0.41                                                            
             2  -- -- 200  8.2 --     en masse                            
B    1.24 0.41                                                            
             0.47                                                         
                2.5                                                       
                   -- 250  14.9                                           
                               1.9    50                                  
C    1.47 -- 2.1                                                          
                -- -- 250  6.1 --     en masse                            
D    3.37 -- 0.46                                                         
                0.48                                                      
                   2.5                                                    
                      300  9.6 1.9    50                                  
E    4.17 -- 0.41                                                         
                1.9                                                       
                   -- 250  8.1 2.4    150                                 
F    4.08 -- 2.6                                                          
                -- -- 200  1.0 1.8    300                                 
G    1.35 -- 0.42                                                         
                2.2                                                       
                   -- 250  10.5                                           
                               1.9    80                                  
__________________________________________________________________________
 
    
     It can be seen from Tables 1, 1a, 1b and 1c that the compositions forming the object of the present invention have a very high general performance level with respect to their mechanical properties and retain these performances well despite oxidation. The antioxidant properties are also excellent. 
     EXAMPLE 33 
     Lubricant compositions are prepared by adding to a 10W30 oil the product prepared in Example 2, above, in different concentrations. 
     These compositions are tested in accordance with the methods described in the preceding example. These lubricant compositions are also tested on a Four-ball machine under a load of 150 kg. The results of these tests appear in Table 2, below. 
     
                                           TABLE 2                                 
__________________________________________________________________________
Mechanical Properties                                                     
                             After                                        
Before Oxidation             Oxidation                                    
% by Four-Ball Test          Seizure                                      
                                    Oxidation                             
Weight                                                                    
     Seizure imprint in mm.                                               
                    Welding                                               
                         Falex                                            
                             imprint                                      
                                    Increase                              
of   70 90 110                                                            
              130                                                         
                 150                                                      
                    load in  in     in                                    
Product                                                                   
     kg.                                                                  
        kg.                                                               
           kg.                                                            
              kg.                                                         
                 kg.                                                      
                    kg.  mm. mm.-100 Kg.                                  
                                    Viscosity                             
__________________________________________________________________________
0.5  -- 0.48                                                              
           0.5                                                            
              1.1                                                         
                 -- 200  2.7 1.8    50                                    
1.35 -- 0.48                                                              
           0.49                                                           
              0.9                                                         
                 2.5                                                      
                    250  3.3 2      30                                    
2.5  -- 0.48                                                              
           0.49                                                           
              0.7                                                         
                 1.1                                                      
                    250  3.9 1.8    30                                    
4    -- 0.48                                                              
           0.50                                                           
              0.5                                                         
                 0.9                                                      
                    250  7.3 2      30                                    
5    -- 0.47                                                              
           0.51                                                           
              0.5                                                         
                 0.55                                                     
                    250   10.6                                            
                             1.8    30                                    
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     It can be seen that these compositions show an excellent general performance level with respect to their mechanical and antioxidant properties, even with a low concentration of additive. 
     The terms and expressions which have been employed are used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the invention claimed.