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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
  • C10M133/56—Amides; Imides
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  • C08F8/00—Chemical modification by after-treatment
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/027—Neutral salts thereof
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  • C10M2207/02—Hydroxy compounds
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
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  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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  • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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Definitions

• the invention relates to additives for lubricating compositions and also to lubricating compositions containing the additives.
• the additives with which this invention is concerned are detergents which are effective cold sludge dispersants.
• deposits may be formed in the engines in two ways and there are two distinct problems involved in keeping the engines clean.
• One problem is the deposition of soot, lacquers and other deposits, mainly in the pistonring zone, under high speed, and consequently high temperature, operating conditions. These deposits may arise from partial combustion productsof the fuel or as the result of the oxidation or thermal degradation of the lubricant or both.
• This problem is alleviated by the addition to the lubricating oil of what are known in the art as high temperature detergents, conventional detergents or normal detergents.
• the other problem is the deposition of another kind of dirt. This dirt has become known as cold sludge. cold weather and under driving conditions obtaining in cities and in other conditions when the engines never truly warm up. This latter problem is alleviated by the addition to the lubricant of additives known as cold sludge dispersants. Cold sludge is derived almostentirely from the fuel andis normally wet.
• the conventional detergents have in general been metal containing derivatives Oforganic compounds such as basic alkaline earth metal petroleum or alkyl benzene sulphonates, basic alkaline earth metal salts of phosphosulphurised polybutenes or alkaline earth metal phenates.
• the cold sludge dispersants have in general been copolymers of polar monomers such as N-vinyl pyrrolidone with oil solubilising copolymerisable monomers such as long-chain alkyl methacrylates.
• products having useful detergent and cold sludge dispersant properties have been obtained by reacting a long chain monoalkenyl succinic anhydride, preferably polyisobutenyl succinic anhydride, with polyamines such as polyethylene polyamine or ,B-aminoethyl piperazine.
• a long chain monoalkenyl succinic anhydride preferably polyisobutenyl succinic anhydride
• polyamines such as polyethylene polyamine or ,B-aminoethyl piperazine.
• an additive for lubricating compositions which additive is a reaction product of (a) a long-chain monoalkenyl succinic anhydride, and (b) a reaction product of dicyandiamide with a primary alkylene polyamine having at least two primary amino groups and atleast one primary or secondary amino group from two to four carbon atoms removed from one of the primary amino groups.
• the novel additives of the present invention are high temperature detergents, and may also be cold sludge dispersants. It is preferred to use additives which have both properties.
• the additive will generally have a nitrogen content
• Cold sludge is formed in engines in 3,338,831 Patented Aug. 29, 1967 sired degree of cold sludge dispersancy or detergency;
• the long chain-mono-alkenyl succinic anhydride may be obtained from the reaction between a normally liquid oil-soluble polyolefin having a molecular weight of from 700 to 3000, preferably from 750 to 1500, and maleic anhydride.
• a normally liquid oil-soluble polyolefin having a molecular weight of from 700 to 3000, preferably from 750 to 1500, and maleic anhydride.
• the polyolefin is polyisobutylene.
• Reaction product (b) is prepared by reaction between dicyandiamide, otherwise known as cyanoguanidine, and a primary alkylene polyamine having at least two primary amino groups and at least one primary or secondary amino group not less than two carbon atoms and not more than four carbon atoms removed from one of the primary amino groups at a temperature of at least C. and preferably between 240 and 280 C.
• the molar ratio of reaction product (a) to reaction product (b) may be varied from 1:1 to 5:1, preferably from 1:1 to 3:1, depending on the number of reactive nitrogen atoms in (b). In general 1:1 molar ratios are preferred, although when polyamines having molecular weights in excess of about 500 are employed it will be necessary to use a higher molar ratio of (a) to (b).
• the alkylene polyamine has the general formula H H(RNH) -RNH2 where R is an alkylene radical, preferably CH CH and n is an integer from 1 to 5 or more.
• alkylene polyamines examples include diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine and mixed higher poly-' ing narrow ranges of molecular weights, those indicated being the most useful in this invention.
• Another polyamine which is useful in this invention is one marketed by Union Carbide Limited under the name of Polyamine D dominantly a mixture of isomeric polyethylene hexamines of formula C H N and related hexamines containing piperazine rings and 12 C atoms.
• the average molecular weight of the mixture is approximately that of pentaethylene hexamine, i.e. 233, and the mixture contains a predominance of amines having 24 primary amino groups and at least two secondary amino groups.
• the additives of this invention may be prepared by heating together the long chain alkenyl succinic anhydride (a) and the reaction product (b), at such a temperature as to remove the water of reaction and for sufiicient time to allow reaction to take place.
• reaction product (b) which is stated to be pre
• the chemical nature of the reaction product (b) is not known with certainty and a mixture of products is normally formed.
• At 130 C. fairly rapid exothermic reaction takes place with evolution of ammonia.
• molar ratios of dicyandiamide to polyalkylenepolyamine of from 6:5 to 3:5 may be used.
• Preferably a molar ratio of 1:1 is employed.
• the molar ratio of polyalkylene polyamine to dicyandiamide exceeds 1:1 it may be necessary to strip off excess of polyalkylene polyamine under vacuum prior to reacting with reaction product (a).
• reaction product (b) is normally carried out by simply heating the two reactants together although solvents may be used, for example, water. However, when water is used as the solvent the resultant product is lower in nitrogen than when the reaction is carried out without a solvent, due to hydrolysis.
• the lubricating compositions of this invention may exhibit adequate cold sludge dispersancy and high temperature detergency by the incorporation therein of quite small amounts of the additive, and the compositions may contain, for example, 0.1 to 10% by weight of the additive, and, preferably, from 0.5 to 5.0% on the weight of the composition. However, in some cases, particularly in the case when a lubricating oil concentrate is required, it may be desirable to use concentrations greater than 10%.
• the lubricating compositions of the present invention may contain also copper deactiva tors, pour-point depressants, antioxidants, viscosity index improvers and other conventional additives as necessary.
• antioxidants which may be used in conjunction with the additives of the present invention are the metal salts of dialkyl or di(alkaryl) or alkylalkaryl dithiophosphates, especially the zinc salts of dialkyl dithiophosphoric acids derived from C C alcohols.
• the dithiophosphate may be present in the composition in amounts from 0.2 to 2% and preferably from 0.5 to 1.5% by weight based on the weight of the composition.
• This product therefor contained 79.5% of polyisobutenyl succinic anhydride.
• Section B The reaction between tetraethylene pentamine and dicyandiamide 189 gm. (1 mole) of tetraethylene pentamine and 84 gm. (1 mole) of dicyandiamide were stirred together in a 500 ml. flask heated by a mantle and fitted with a mechanical stirrer, reflux water condenser and a nitrogen bleed. The temperature was slowly raised to C. during half an hour, when the dicyandiamide slowly dissolved and ammonia was evolved vigorously. The temperature of the orange-yellow slurry was then raised to 240-260 C. and kept there for 9 /2 hours. The product was a clear brown liquid at this temperature, but set to a brittle brown solid on cooling.
• Section C.Preparation of a typical additive 0) the present invention 9.35 gm. of the product of Section B were stirred with 144.0 gm. of the product of Section A (2) in a beaker heated in an oil bath at 20 C. and blown with a slow nitrogen stream. After 8 hours, 153 gm. of Mineral Oil A were stirred in, a clear 50% solution of the additive in mineral oil thus being obtained.
• additives according to the present invention were prepared in a substantially similar manner to that in Example I, and the essential features of the reactions are presented in Table I.
• the polyisobutenyl succinic anhydride intermediates were all prepared as in Example I A(2), although in some cases it was not considered necessary to treat with hexane.
• the reaction products (b) were all prepared by heating the amine with dicyandiamide at 280 C. for 8 hours except where otherwise indicated.
• He additives of the present invention were prepared by heating the polyisobutenyl succinic anhydride and reaction product (b) at 200 C. for about 8 hours after which time the additional mineral oil, which was a spindle oil having a viscosity of about 52 seconds Redwood I at 140 C., was added and the 50% concentrate then filtered.
• a quantity of cold sludge was collected from a Lauson engine which had been run deliberately under low temperature conditions using a leaded petrol and, as the lubricant, a plain mineral oil free from additives.
• This sludge was an emulsion containing from about to about 50% of water, the remainder containing from 0.8- 4.0% of lead, from 3-10% of material insoluble in pentane and from 140% of material insoluble in benzene, all percentages being by weight.
• the sludge (1 gram) was shaken for 30 minutes with 20 ml-s. of a light spindle oil having dissolved therein the additive under test on an automatic shaking machine and then poured into a measuring cylinder with a tapered base which was allowed to stand in an oven at 60 C.
• the oil sample (250 ml. approx.) was contained in a sump which was fed by a chicken feed to maintain a constant level of oil.
• the oil was splashed continuously for 24 hours by means of Wires on a rotating spindle on to a heated sloping aluminium panel maintained at 275 C.
• Typical lubricating oil blends of the present invention are given in the following examples, all percentages being by weight on the weight of the total composition.
• Mineral oil A was a solvent refined mineral oil having a viscosity of about 160 seconds Redwood I at 140 F.
• Mineral oil B was a mineral oil having a viscosity of about seconds Redwood I at F.
• Mineral oil C- was a spindle oil having a viscosity of about 52 seconds Redwood I at 140 F.
• Mineral oil blend D was a blend consisting of 87.5%
• ZDDP 1 was a mineral oil concentrate of mixed zinc dialkyl dithiophosphates derived from isopropanol and methyl isobutyl carbinol whilst ZDDP 2 was an essentially similar zinc dithiophophate derived from isopropanol and capryl (l-methyl heptyl) alcohol.
• the concentrates contained about 8.0% of phosphorus.
• Additive A was the barium salt of a phosphosulphurized polyisobutylene of molecular weight about 1000, the neutralization having been effected in the presence of an alkyl phenol, followed by treatment with carbon dioxide.
• the V1. Improver employed was a copolymer of longchain alkyl methacrylates with n-butyl methacrylate, used as a 14% concentrate in mineral oil.
• Examples 34 and 35 were suitable for use as I.C. engine oils and conformed to the Society of Automotive Engineers (SAE) 30 classification.
• Examples 37, 38 and 39 were multigrade oils of the SAE 20W/ 30 type, Examples 37 and 38 being designed to have a performance level equivalent to that required by US Specification MIL-L-2104A and British Ministry of Defense Specification DEF 2101B, whilst Example 39 was designed to have a performance equivalent to that required by MIL-L-2l04A Supplement 1.
• Examples 36 and 40 were multigrade oils of the SAE 10W/30 type, the latter being designed to have a performance level equivalent to that required by MIL-L- 2104A Supplement 1.
• Test duration 36 hours. Speed 1500:15 r.p.m. B.H.P About 3.3. Sump temperature 280 F. Coolant outlet temperature 302i2 F. Coolant inlet temperature 299 '-2 F. Fuel PE/IP reference gasoline.
• the AT-4 conditions are specified in the Institute of Petroleum Standards for Petroleum and its Products: Method IP 175/ 601". The results of these tests are summarized in Table IV.
• blowby Nil 240 240 240 Uncontrolled-" 240 240 2nd hour Rising to 210 240 240 3rd-5th hours 210 240 240 6th hour Falling to own 240 240 level (no heat- Duration hours 3 x 6 12 2
• exhaust gas was fed in from a by pass into the crankcase breather at a slight pressure.
• the degree of ventilation necessary to produce a standard amount of blowby was determined during the run-in period by taking blowby readings at one minute intervals using a large gasmeter. The blowby was checked every 6 hours during the test and any necessary adjustments made.
• compositions P and Q were both SAE 20W/ 30 oils having similar physical properties to Examples 37, 38 and 39 and have the following compositions:
• the dispersant V.I. Improver was a commercially available o-il concentrate of a copolymer derived from long chain fumarates, vinyl acetate and N-vinyl pyrrolidone.
• lubricating oils of the present invention were markedly superior to the plain mineral oil and to the prior art compositions particularly in respect to overall engine cleanliness and the weight of sludge in the sump.
• additives of the present invention in addition to being ashless and having good dispersant properties at high temperatures equivalent to those of commercially available metallic detergents may also have good cold sludge dispersing properties.
• the additives of the present invention may have significantly improved corrosion inhibiting properties compared to other succinimide derivatives of the prior art.
• reaction product (b) the mole ratio of amine to dlcyandiamide was 1:1 except in the case of Example 18 where the ratio was 6: 5.
• Example 16A Base oil 165 D- Basic barium 3.7 0.9 2) 64.7 0- The numbers (I) or (2) 1n the ZDDP column are to gg f identify the actual zinc dithiophosphate antioxidant used f-g g-g i.e. ZDDP-1 or ZDDP-2. 2:0 0:9 (1 :1 11-
• the additive of Example 16A was prepared in the same 28 8:3 5 i: manner as that of Example 16 except that reaction prod- 6.0 0.9 (1) 27.4 5+ ucts (a) and (b) were reacted in 1:1 molar ratio instead 23 3;; g; 5 45 of 4:1.
• the product contained 2.36% N.
• 2.0 0.9 (2) 64.2 B 1.0 0.7 (1) 44.2 B 2.0 0.9 (1) 27.7 B 2.0 0.7(1) 62.0 B s 11 a 212 11 2.
• a lubricating composition comprising a major proportion of a lubricating oil and from 0.1% to 10% by weight of a second reaction product of (a) a long chain mono-alkenyl substituted succinic acid or anhydride, said long chain mono-alkenyl substituent having a molecular weight of at least 700, with (b) a first reaction product of dicyandiamide with a primary alkylene polyamine having at least two primary amino groups and at least one primary or secondary amino group from two to four carbon atoms removed from one of the primary amino groups, said first reaction product being prepared by heating said dicyandiamide with said polyamine at a temperature of from about 130 C. to 280 C. and said second reaction product being a condensation reaction product.
• a lubricating composition as claimed in claim 1 wherein the primary alkylene polyamine has the formula H N-(RNH), -RNH where R is an alkylene radical having from 2 to 4 carbon atoms and n is an integer of from 1 to 5.
• An additive as claimed ethylene and n is from 2 to 4.
• reaction product (b) is obtained from a reaction mixture containing a molar ratio of dicyandiamide to primary alkylene polyamine of from 6:5 to 3:5.
• a lubricating composition as claimed in claim 1 containing from 0.5% to 5.0% by weight of the additive.
• a lubricating composition as claimed in claim 1 containing from 0.2% to 2.0% by weight of a metal salt of a dialkyl or a di-(alkaryl) or an alkyl-aryl dithiophosphate.
• a lubricating composition as claimed in claim 1 containing also as a viscosity index improver a copolymer of a long chain alkyl methacrylate with a heterocyclic nitrogen-containing monomer.
• a lubricating composition comprising a major proportion of a mineral oil of lubricating viscosity, from 0.2% to 2.0% by weight of a zinc dialkyl dithiophosphate, the alkyl groups containing from 3 to 10 carbon atoms, and from 0.5 to 5.0% by weight of the condensation reaction product of (a) a polyisobutylene substituted succinic acid or anhydride wherein the polyisobntylene substituent has a molecular weight of from 750 to 1500, with (b) the reaction product prepared by reacting, at a temperature of from about C. to 280 C., di-
• the condensation reaction product having been obtained by reacting the reactants (a) and (b) together in a molar ratio of from 1:1 to 5:1.

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• 1964
  • 1964-07-09 GB GB28456/64A patent/GB1068235A/en not_active Expired
• 1965
  • 1965-07-07 BE BE666544A patent/BE666544A/xx unknown
  • 1965-07-08 NL NL656508794A patent/NL139039B/xx unknown
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  • 1965-07-08 US US470564A patent/US3338831A/en not_active Expired - Lifetime
  • 1965-07-08 FR FR23871A patent/FR1450694A/fr not_active Expired
  • 1965-07-09 DE DE19651594380 patent/DE1594380A1/de active Pending

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