Classifications

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  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/06—Phosphorus compounds without P—C bonds
  • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
  • C07F9/165—Esters of thiophosphoric acids
  • C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
  • C07F9/1656—Compounds containing the structure P(=X)n-X-C(=X)- (X = O, S, Se; n = 0, 1)
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Definitions

• a lubricant composition comprises a major amount of lubricating oil and a minor amount of one or more oilsoluble dithiophosphoric acid derivatives having the general formula:
• R is a monoor di-valent aliphatic or aromatic group
• X is an oxygen or sulphur atom
• R is an alkyl group
• R and R are the same or different and are alkyl, alkaryl, aryl or aralkyl groups or alkenyl and n is 0 when R is a monovalent group or is 1 when R is a divalent group.
• dithiophosphoric acid derivatives certain of v which are novel compounds, function as antioxidants, load carrying and antiwear additives in the lubricant compositions.
• This invention relates to lubricants and in particular to lubricants containing S-carbamoyl dithiophosphates.
• Ar is arylene of from 6 to 12 carbon atoms and R is a hydrocarbyl group, substantially free of aliphatic unsaturation, having from 12 to 30 carbon atoms.
• dithiophosphate lubricant additives in addition to possessing antioxidant, loadcarrying and antiwear properties, should not be unduly prone to form deposits in oil solution at the elevated temperatures at which internal combustion engines are normally operated. e.g., up to 130C.
• the present invention provides lubricants containing ash-free dithiophosphoric acid derivatives, some of which are novel compounds, having a reduced tendency to form deposits composed of oil-insoluble diisothiocyanate decomposition products.
• the present invention provides a lubricant composition
• a lubricant composition comprising a major amount of lubricating oil and a minor amount of one or more oilsoluble dithiophosphoric acid derivatives having the general formula:
• R 's" A wherein R is a monoor di-valent aliphatic or aromatic group; X is an oxygen or sulphur atom; R is an alkyl group; R and R are the same or different and are alkyl, alkaryl, aryl or aralkyl groups or alkenyl and n is 0 when R is a monovalent group or is 1 when R is a divalent group.
• the additives of the present invention may contain as a contaminant. a small proportion of isothiocyanate decomposition products.
• the groups R and R are preferably alkyl, alkaryl or aralkyl groups. and may contain from l to 30, preferably 4 to l8, carbon atoms.
• the group R may contain from l to 30. preferably 2 to 22. more preferably 4 to l3. carbon atoms.
• the group R is preferably a monovalent alkyl group containing from 1 to 18 carbon atoms or a di-valent aryl'group, optionally bearing one or more alkyl substituents, which contains from 6 to 24 carbon atoms. a
• the dithiophosphoric acid derivatives employed in the lubricants of the present invention may be prepared by reacting an isocyanate compound, as more fully described hereinaftenwith a dithiophosphoric acid.
• the dithiophosphoric acid'starting materials may be prepared by reaction of 1 mole of phosphorus pentasulphide with 4 moles of an alcohol ormixture of alcohols, a phenol or mixture of phenols or a mixture of one or more alcohols and one or more phenols in accordance with techniques well-known in the preparation of the zinc salts of 0,-0-dihydrocarbyl dithiophosphoric acids hereinbefore described.
• the nature of the alcohol and/or phenol employed will determine the nature of the groups'R and R in the additives of the present invention. Examples of alcohols which may be used include:
• ethanol n-propanol isopropanol n-butanol isobutanol amyl alcohol including mixed amyl alcohols mixtures of alcohols, derived from the OX0 process decanol dodecanol lauryl alcohol Suitable phenols include:
• Suitable mixtures of alcohols and phenols include:
• the isocyanate compound which may be employed in the preparation of the additives can be a monoisocyanate, preferably an aliphatic mono-isocyanate, of the formula:
• Suitable mono-isocyanates which may be used to prepare S-carbamoyl dithiophosphates which may be used in the present invention include:
• the isocyanate compound can have the formula:
• lsocyanates of the latter formula may be prepared by reacting one of the isocyanate groups of a di-isocyanate with an alcohol or mercaptan.
• Suitable di-isocyanates include toluene 2,4, diisocyanate, which is particularly preferred.
• di-isocyanates are:
• Compounds which may be reacted with the diisocyanate include:
• the temperature at which the additives of the present invention are prepared may be varied according to the preparative route chosen. In order to obtain the optimum antioxidant performance, load-carrying ability and to minimise deposit formation at elevated temperatures it is preferred to carry out the reaction with the dithiophosphoric acid at about 75 80C., although temperatures of up to 100C. or as low as ambient temperature may be employed. if desired.
• Each of the reactions carried out in the preparation of the additives is conventiently carried out at atmospheric pressure. However, any or all of the reactions may be carried out, if desired, at pressures above or below atmospheric.
• the lubricants of the present invention may contain from 0.1 to preferably from 0.5 to 5%, by weight of the dithiophosphoric acid derivatives.
• the lubricants may also contain other additives of the type conventionally used in lubricants, especially ash-free additives.
• additives include antioxidants and antiwear additives (additional to the dithiophosphoric acid derivatives) and corrosion inhibitors, detergents, dispersants, viscosity index improvers. extreme pressure additives or any combination thereof.
• Suitable additional antioxidants are phenothiazine, optionally substituted on one or both benzene nuclei and/or the nitrogen atom, a hindered phenol or a hindered bis-phenol or a secondary amine having two aromatic nuclei attached to the nitrogen atom.
• the additional antioxidant is a secondary amine having two aromatic nuclei attached to the nitrogen atom, in which one or both of the aromatic nuclei bear one or more alkyl groups, particularly alkyl groups containing from 4 to 12, more preferably 8 or 9, carbon atoms.
• Examples of such amines are monooctyl phenyl-a-naphthylamines and mono-octyl phenyl-B-naphthylamines, particularly N-p-t-octyl phenyl-a-naphthylamine and N-p-t-octyl phenyl-finaphthylamine; and mono-nonyl phenyl-anaphthylamines and mono-nonyl phenyl-B- naphthylamines.
• amines are diphenylamine and monoor di-alkyl diphenylamines, particular examples being di-octyl and di-nonyl diphenylamines, especially the p-p isomers. These secondary amines may be used in an amount of from 0.1% by weight, preferably 0.2% to 5% by weight.
• ash-free antioxidants which may be used include the trithiopyrophosphate additives described in British Pat. No. 1,254,554, and in German Offenlegungsschrift No. 2,162,180 and copending United States application Ser. No. 252,254 filed May 11, 1972.
• Suitable corrosion inhibitors include benzotriazole or a derivative thereof, an aliphatic carboxylic acid, a dicarboxylic acid, for example, dodecenyl succinic acid, mercaptobenzothiazole and benzothiazole disulphide.
• Suitable detergents include an alkaline earth metal petroleum or alkyl benzene sulphonate, carboxylate, salicylate or naphthenate, any of which may be overbased with an alkaline earth metal carbonate.
• Other suitable detergents, which may also be overbased, include a phosphosulphurised hydrocarbon and an alkyl phenol which has been neutralised by an alkaline earth metal base.
• a suitable dispersant is a long chain hydrocarbon substituted by a polyamine group attached thereto either directly or through an amide or imide link, as described in British Pat. Nos. 1,068,235 and 1,121,641.
• a typical viscosity index improver which may be used in this invention is a copolymer of a mixture of monomers, which monomers are esters of acrylic or methacrylic acid.
• Other unsaturated monomers such as N- vinyl pyrrolidone, diethylamino-ethyl methacrylate or fumaric acid may be included in the mixture to give viscosity index improvers having dispersant properties.
• dithiophosphoric acid derivatives which can be diluted with additional lubricating oil before being used.
• these more concentrated solutions may be oil concentrates or additive packages, i.e., may be, respectively concentrated solutions of one or more dithiophosphoric acid derivatives or concentrated solutions of mixtures of one or more dithiophosphoric acid derivatives and one or more known additives.
• an oil concentrate or additive package comprising from 10% to more preferably 20% to 50%, by weight of a lubricating oil having dissolved therein from 90% to 30%, more preferably to 50%, by weight of one or more of the dithiophosphoric acid derivatives, optionally together with one or more known additives.
• the lubricating oil employed in the lubricants, oil concentrates and additive packages of the present invention may be a mineral oil of lubricating viscosity of well-known type.
• a synthetic ester-based oil may be used as the lubricating oil. Suitable synthetic ester oils are described in British Pat. Nos. 930,136 and 1,205,177.
• dithiophosphoric acid derivatives employed in the lubricants are novel compounds.
• the present invention therefore includes in another aspect novel dithiophosphoric acid derivatives suitable for use as lubricant additives, having the general formula:
• R, R R as a di-valent group, R and X are as hereinbefore defined.
• R, R R as a di-valent group, R and X are as hereinbefore defined.
• the present invention further provides a process for the preparation of a dithiophosphoric acid derivative, which process comprises reacting a compound of the formula:
• the invention also includes a dithiophosphoric acid derivatives when produced by either of the above processes.
• EXAMPLE 1 Ethyl isocyanate (13.8g. 0.2m) was added dropwise to stirred di-tridecyl dithiophosphoric acid (110g.
• EXAMPLE a Toluene di-isocyanate 174g, 1.0m) was heated to approximately 105C. and 0,0-di-isobutyl dithiophosphoric acid (250g. 1.0m) run in over /4 hour and left to react for a further 2 /4 hours at 105C.
• Tridecanol (40.0g., 0.2m.) was added to toluene diisocyanate (34.8g.. 0.2m.) over /2 hour at a temperature of 7080C. and the product stirred for a further V2 hour.
• To the product was then added 0,0'-di-isobutyl dithiophosphoric acid (55.6g., 0.2m.) over /4 hour followed by a further 4.0g. (10%) of tridecanol and the reaction continued for a further one hour to yield 1 19g. (95% of an olive green liquid containing 5.00%? (theory 5.04%
• EXAMPLE 9 An 0,0-dialkyl dithiophosphoric acid was prepared by reaction of P 5 with Alfol 20-22 (a commercially available mixture of alcohols containing 20-22 carbon atoms). To toluene di-isocyanate (34.8g., 0.2m.) was added, in bulk. 2-ethylhexanol (26g, 0.2m.), causing an exotherm. To the product was added the 0,0'-di- Alfol 20-22 dithiophosphoric acid (150g.,0.2m.), after melting. causing the temperature to rise to 50C. The total addition time of the dithiophosphoric acid was hour. after which the reaction was continued for a further 1 /2 hours to yield 205g. (97.5%) of a grey/green solid containing 2.77%P (theory 2.93%).
• EXAMPLE 10 a. lsobutanol (74.0g., 1.0m.) was added dropwise to toluene di-isocyanate 174g, 1.0m.) over 1: hour, during which time the initial temperature of 30C. rose to C. due to the strong exotherm. The reaction was continued, with stirring, for a further one hour.
• EXAMPLE 12 EXAMPLE l3 lsobutanol l4.8g., 0.2m. was added in bulk to toluene di-isocyanate (69.6g., 0.4m.) and reacted for one hour at 30-45C. 0,0-di-2-ethylhexyl dithiophosphoric acid (76.8g., 0.2m.) was added dropwise over 1 hour at 30C. and reaction contined for /2 hour. To 129g. of the resulting product was added.
• Example 17 The procedure of Example 16 was repeated using toluene di-isocyanate (69.6g., 0.4m.) and Alfol 6 (40.8g., 0.4m.) (with a strong exotherm to 80C.), and 0,0-ditridecyl dithiophosphoric acid (216g, 0.4m.) to yield 32 l g. (98.5%) of a light green viscous liquid containing 3.95%P (theory 4.03%).
• Example 18 The procedure of Example 16 was repeated using toluene (ii-isocyanate (69.6g., 0.4m.), 2-ethylhexanol (520g, 0.4m.), and 0,0-di-tridecyl dithiophosphoric acid (216g, 0.4m.) to yield 327g. (98%) ofa very light green mobile liquid containing 3.74%? (theory 3.89%).
• Example 19 The procedure of Example 16 was repeated using toluene di-isocyanate (696g, 0.4m.) 3,5,5- trimethylhexanol (57.6g., 0.4m.), and 0,0-di-isobutyl dithiophosphoric acid (106.8g., 0.4m.) to yield 21 lg. (90.5%) of a light green solid containing 5.63%? (theory 5.22%).
• EXAMPLE 20 isodecanol (79g, 0.5m.) was added to toluene diisocyanate (87g, 0.5m.) over A hour. The initial temperature was 50C., exotherming strongly to a maximum 105C. The reaction mixture was cooled to 80C. and stirred for a further 1 1 hour. 0,0'-di-isobutyl dithiophosphoric acid 134g., 0.5m.) was then added over A hour, keeping the temperature at 7580C., and the mixture stirred for a further 14 hour, whereafter isodecanol (7.9g, was added to ensure completion of reaction. There was obtained 201g. (96%) of a light green fairly mobile liquid containing 5.3%P (theory 5.4%).
• EXAMPLE 21 In a manner identical to Example 20, except that a dry nitrogen stream was passed through the reaction mixture to prevent moisture absorption by toluene diisocyanate, there was prepared from toluene diisocyanate (435g, 2.5m.), isodecanol (395g, 2.5m.)
• EXAMPLE 22 This was a repetition of Example 21, identical in every respect, and the product contained 5.3%P and 12.0%S.
• EXAMPLE 23 An 0,0'-di-P1B phenyl dithiophosphoric acid was prepared from P S and a polyisobutenyl substituted phe-' EXAMPLE 24 Phenyl isocyanate (23.8g., 0.2m.) was weighed carefully into a flask and 0,0'-di-isobutyl dithiophosphoric acid (52.6g., 0.2m.) slowly added thereto. The resulting reaction was vigorously exothermic, causing a maximum temperature of 90C. to be obtained. Stirring was continued for hour and the final product was a dark green liquid.
• the products of a number of the preparations exemplified above were tested by means of the Timken O.K. load test in accordance with the Institute of Petroleums Test Method IP/240/69.
• the apparatus employed comprises a roller mounted on a spindle, the roller being rotated against a seated metal block lubricated with the test blend.
• a lever system mounted on the spindle is also mounted on the spindle, the weight being increased until the test blend fails as judged by scoring of the seated metal block.
• the blends tested consisted of sufficient of the test additives to provide a phosphorus content of 0.072% by weight in a base oil which was 150 Solvent Neutral mineral oil having viscosities of about 33 and 5 cSt at 100F. and 210F. re spectively.
• the base oil alone had a Timken O.K. load of 12 lbs. and the results obtained with the various test additives are as set out above in each relevant example.
• Typical results obtained in this test with the widely used zinc 0.0-di-hydrocarbyl dithiophosphates, at 0.08% by weight phosphorus level, are 33 lbs. (hydrocarbyl mixed isobutyl and pentyl groups), 35 lbs.
• Base Oil only 45 min. Base oil product of Example 1. 122 min. Base oil product of Example 2. 78 min. Base oil product of Example 3. 402 min. Base oil product of Example 26. 129 min. Base oil product of Example 27. 88 min.@ Base oil Additive 4. 405 min. Base oil Additive 2. 298 min. Base oil Additive 3. 82 min.@ Base oil Additive 5. 124 min.
• Solvent Neutral mineral oil having viscositics of about 1 l0 and 11 C51. at 100F. and 210F. respectively. em 25 p.s.i. loss.
• sintered glass crucibles had been cleaned, flushed through with acetone, dried in an oven at 100C. for about /2 hour, cooled in air and weighed.
• each blend was poured into approximately 200ml. of heptane and the resulting mixture filtered as quickly as possible through a crucible.
• the crucible contents were then thoroughly rinsed with clean heptane to ensure all oil was removed, then dried in the oven for about /2 hour, cooled in air and re-weighed.
• the results obtained were expressed as the weight of precipitate collected/weight of additive in blend X 100% In this way were evaluated blends containing one of the aforesaid prior art additives and blends containing the product of Example 25, the results being as follows:
• a composition according to claim 1 containing 1.
• a lubricant composition consisting essentially of lubricating oil having dissolved therein from about 0.1 to 10% by weight of at least one oil-soluble dithiophosphoric acid derivative having the general formula:
• R is selected from the group consisting of mono-valent aliphatic groups, mono-valent aromatic groups. di-valent aliphatic groups and di-valent aromatic groups;
• X is selected from the group consisting of oxygen atoms and sulphur atoms;
• R is an alkyl group;
• R and R are the same or different and are selected from the group consisting of alkyl groups, alkaryl groups, aryl groups, aralkyl groups and alkenyl groups; and
• n is 0 when R is a mono-valent group and n is I when R is a divalent group.
• R and R are selected from the group consisting of alkyl, alkaryl and aralkyl groups containing from 4 to 18 carbon atoms.
• R is selected from the group consisting of a mono-valent alkyl group containing from I to 18 carbon atoms and a divalent aryl group.
• R is a divalent aryl group bearing at least one alkyl substitutent and containing from 6 to 24 carbon atoms.
• R is selected from the group consisting of mono-valent aliphatic groups, mono-valent aromatic groups, di-valent aliphatic groups and di-valent aromatic groups
• X is selected from the group consisting of oxygen atoms and sulphur atoms
• R is an alkyl group
• R and R are the same or different and are selected from the group consisting of alkyl groups, alkaryl groups, aryl groups, aralkyl groups and alkenyl groups
• n is 0 when R is a mono-valent group and n is 1 when R is a di-valent group.

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• 0
  • BE BE785885D patent/BE785885A/fr unknown
• 1971
  • 1971-07-06 GB GB3163471A patent/GB1385324A/en not_active Expired
• 1972
  • 1972-07-05 NL NL7209386A patent/NL7209386A/xx unknown
  • 1972-07-05 DE DE2233010A patent/DE2233010A1/de active Pending
  • 1972-07-05 US US00269205A patent/US3844963A/en not_active Expired - Lifetime
  • 1972-07-05 IT IT26666/72A patent/IT962802B/it active
  • 1972-07-05 BR BR4432/72A patent/BR7204432D0/pt unknown
  • 1972-07-05 FR FR7224243A patent/FR2144778A1/fr not_active Withdrawn
  • 1972-07-05 AU AU44269/72A patent/AU4426972A/en not_active Expired
  • 1972-07-05 CA CA146,341A patent/CA990268A/en not_active Expired

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