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  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C10M2223/04—Phosphate esters
  • C10M2223/045—Metal containing thio derivatives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/251—Alcohol-fuelled engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/255—Gasoline engines
  • C10N2040/28—Rotary engines
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• the present invention relates to reaction products of polyenes, a process for their preparation, lubricating oil compositions, fuel compositions and additive concentrates containing them and their use as dispersant additives.
• European Patent Application No. 94200496.1 describes the use, as dispersant additives in lubricating oils (luboils), of mono- and bis-cyclopentadiene derivatives of the general formula in which R1 and R2 each represent a hydrogen atom, or together represent a carbon-carbon single bond; each of R4 and R5 independently represents a hydrogen atom, or a C1-C20 alkyl or phenyl group, each of which may be optionally substituted; R6 represents a hydrogen atom, or a C1-C20 alkyl or phenyl group, each of which may be optionally substituted and R7 represents a group -CH2-NHR8 in which R8 represents an optionally substituted alkyl group, or a group -COX wherein X represents an optionally substituted alkoxy group or -NHR8 where R8 is as defined above; or R6 and R7 together represent a group where R8 is as defined above; x is 1 to 6, preferably 1 to 4; and each R3
• the acylating reagent (A) is the reaction product of (B) a C4-C20 polyene or oligomer prepared therefrom and (C) an ethylenically unsaturated carboxylic reagent.
• the reaction is conveniently carried out in the presence of a suitable solvent at elevated temperature (i.e. above ambient temperature (20°C)), e.g. in the temperature range 25 to 200°C, often under reflux conditions and, where necessary, at elevated pressure, e.g. in the range from 2 to 100 x 105 Pa .
• solvents examples include hydrocarbon solvents such as hexane, cyclohexane, toluene and xylene; ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; alcohols such as 1-pentanol (amyl alcohol) and 2-methyl-2-propanol (tert-butyl alcohol); and chlorohydrocarbons such as dichloromethane.
• hydrocarbon solvents such as hexane, cyclohexane, toluene and xylene
• ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane
• amides such as dimethylformamide and dimethylacetamide
• nitriles such as acetonitrile
• alcohols such as 1-pentano
• Reagent (B) is a C4-C20, preferably C4-C18, more preferably C4-C16 and especially C5-C12, polyene or oligomer prepared therefrom.
• the polyene contains two or more, preferably two (2) to four (4) carbon-carbon double bonds.
• Particularly preferred polyenes are those containing three (3) carbon-carbon double bonds (trienes), and especially two (2) carbon-carbon double bonds (dienes).
• C4-C20 polyenes include 1,5-hexadiene, 1,7-octadiene, 1,9-undecadiene, (di)cyclopentadiene, norbornadiene, 1,2,4-trivinylcylcohexane, 1,3,5,7-cyclooctatetraene and 1,5,9-cyclododecatriene; (di)cyclopentadiene is the most preferred polyene.
• the polyenes may be used as such or in the form of oligomers.
• oligomer denotes a homooligomer or co-oligomer of a diene, comprising at least two diene monomer units.
• the oligomers may have number average molecular weights (M n ) up to 3000, e.g. in the range from 100 to 3000, preferably from 200 to 2500, more preferably from 300 to 2000 and especially from 400 to 1500.
• Preferred oligomers are co-oligomers obtainable by reacting (di)cyclopentadiene or a cyclopentadienylide, e.g. an alkali metal, preferably sodium, cyclopentadienylide, with a compound of the general formula RL m (i) wherein m is an integer from 2 to 6, R represents a hydrocarbyl group or a polyoxyalkylene group, each of which contains from 2 to 30, preferably from 4 to 22, more preferably from 4 to 12 and advantageously from 5 to 8, carbon atoms and L represents a leaving group.
• the group R is preferably an alkyl or xylyl group.
• the leaving group, L may, for example, be a mesylate, tosylate or hydroxyl group but is preferably a halogen atom, particularly a chlorine atom.
• Examples of compounds of formula (i) include ⁇ , ⁇ '-dihaloxylenes (e.g. ⁇ , ⁇ '-dibromoxylene, ⁇ , ⁇ '-dichloroxylene), ⁇ , ⁇ ', ⁇ '-trihalomesitylenes (e.g. ⁇ , ⁇ ', ⁇ ''-trichloromesitylene), pentaerythrityl tetrabromide, C6 or higher dihaloalkanes (e.g.
• Preparation of the oligomers may conveniently be carried out at low temperature, e.g. from -5 to 5°C, in the presence of a suitable solvent, e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
• a suitable solvent e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
• a suitable solvent e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
• a phase transfer catalyst such as that commercially available under the trade mark "Adogen 464".
• the ethylenically unsaturated carboxylic reagent (C) contains a total of at least 3 carbon atoms, preferably a total of from 3 to 50, more preferably from 3 to 30, still more preferably from 4 to 20, and even more preferably from 4 to 10, carbon atoms.
• the ethylenically unsaturated carboxylic reagent (C) may be an alpha-beta olefinic unsaturated carboxylic reagent as described in Page 6, lines 15 to 48 of EP-B-0285609 or Page 6, lines 11 to 39 of EP-B-0287569, e.g.
• anhydrides e.g. maleic anhydride (C4), glutaconic anhydride (C5), itaconic anhydride (C5), citraconic anhydride (
• the ethylenically unsaturated carboxylic reagent (C) is selected from monoethylenically unsaturated C4-C10 dicarboxylic acids and anhydrides, of which maleic anhydride is most preferred.
• the same or different ethylenically unsaturated carboxylic reagents (C) may be used.
• maleic anhydride is used in the preparation of both reagents (A) and (D).
• Reagent (D) is a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent (C), the preparation of which is known in the art.
• reagent (D) is a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent such as maleic anhydride
• it may conveniently be prepared by mixing a polyalkene with a specified amount of maleic anhydride and passing chlorine through the mixture, e.g. as described in GB-A-949,981.
• the derivative may be prepared by reacting thermally, at an appropriate temperature, the polyalkene with a specified amount of maleic anhydride, e.g.
• a particularly preferred process for preparing such a derivative involves reacting the polyalkene with maleic anhydride in a mol ratio maleic anhydride to polyalkene of greater than 1:1, at a temperature in the range from 150 to 260°C and in the presence of a polyaddition-inhibiting amount of a sulphonic acid.
• the polyalkene from which reagent (D) is derived may be a homopolymer or copolymer, for example of at least one C2-C10 monoolefin.
• the polyalkene is a polymer of at least one C2-C5 monoolefin, e.g. an ethylene-propylene copolymer.
• the monoolefin is preferably a C3-C4 olefin, in particular propylene or isobutylene, and preferred polyalkenes derived therefrom include polyisobutylenes and atactic or isotactic propylene oligomers.
• Polyisobutylenes such as that sold by BASF under the trade mark “GLISSOPAL” and those sold by the British Petroleum Company under the trade marks "Ultravis”, “Hyvis” and “Napvis”, e.g. "Hyvis 75", “Hyvis 120", “Hyvis 200” and “Napvis 120" polyisobutylenes,.are especially preferred for use in the present invention.
• the polyalkene has a number average molecular weight (M n ) preferably in the range from 300 to 7000, more preferably from 500 to 5000, still more preferably from 1000 to 4000 and advantageously from 2000 to 3000.
• M n number average molecular weight
• the polyamine (E) contains at least two -NH2 and/or -NH groups, the groups each having at least one active hydrogen thereon.
• Examples of polyamines useful in the present invention are those described in the text from Page 16, line 21 to Page 19, line 53 of EP-B-0287569.
• the polyamine (E) is a compound of the general formula H2N-(CHR1) x -CH2-[A-CH2-(CHR1) x ] y -NH2 (ii) wherein A is -NH or -O-, each R1 independently represents a hydrogen atom or a methyl group, x is in the range 1 to 3, and y is in the range 1 to 10 when A is -NH or y is in the range 1 to 200 when A is -O-.
• each R1 represents a hydrogen atom, and y is in the range 1 to 8; or when A is -O-, then x is 1, each R1 represents a methyl group and y is in the range 1 to 50.
• Reagent (F) is the pre-formed product of reagents (D) and (E) and is prepared according to techniques conventional in the art.
• reagent (D) is a polyalkenyl derivative of maleic anhydride
• reagent (E) is an ethylene polyamine
• they may conveniently be reacted together in a molar ratio of (D) to (E) from 1 - 4:1, in a hydrocarbon solvent at a temperature in the range from 100 to 250°C, e.g. as described in EP-A-0587250.
• the present invention further provides a process for the preparation of a reaction product according to the invention which comprises reacting
• the process may be carried out in the absence of a solvent but is conveniently carried out in the presence of a solvent, e.g. any of those mentioned above, and at elevated temperature (i.e. above ambient temperature (20°C)), for example, in the temperature range 30 to 200°C.
• a solvent e.g. any of those mentioned above
• elevated temperature i.e. above ambient temperature (20°C)
• the process is preferably carried out under reflux conditions.
• the weight ratio of reagent (A) to reagent (D) used in the present process is preferably in the range from 1:2 to 1:1000, more preferably from 1:4 to 1:500, still more preferably from 1:5 to 1:100 and especially from 1:5 to 1:50.
• the weight ratio of reagents (A) plus (D) to reagent (E) (i.e. the ratio of the total combined weight of reagents (A) and (D) to the weight of reagent (E)) used in the present process is preferably in the range from 0.5:1 to 200:1, more preferably from 2:1 to 100:1, still more preferably from 2:1 to 50:1 and especially from 5:1 to 30:1.
• the weight ratio of reagent (A) to reagent (F) used in the present process is preferably in the range from 1:2 to 1:1000, more preferably from 1:4 to 1:500, still more preferably from 1:5 to 1:200 and, advantageously, from 1:10 to 1:100.
• the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) may be used as a dispersant additive in lubricating oils.
• the present invention provides a lubricating oil composition comprising a major amount (more than 50%w) of a lubricating oil and a minor amount (less than 50%w), preferably from 0.1 to 10%w, especially from 0.5 to 5%w (active matter), of a reaction product according to the invention, the percentages by weight being based on the total weight of the composition.
• Suitable lubricating oils are natural, mineral or synthetic lubricating oils.
• Natural lubricating oils include animal and vegetable oils, such as castor oil.
• Mineral oils comprise the lubricating oil fractions derived from crude oils, coal or shale, which fractions may have been subjected to certain treatments such as clay-acid, solvent or hydrogenation treatments.
• Synthetic lubricating oils include synthetic polymers of hydrocarbons, modified alkylene oxide polymers, and ester lubricants, which are known in the art. These lubricating oils are preferably crankcase lubricating oils for spark-ignition and compression-ignition engines, but include also hydraulic lubricants, metal-working fluids and automatic transmission fluids.
• the lubricating base oil component of the compositions according to the present invention is a mineral lubricating oil or a mixture of mineral lubricating oils, such as those sold by member companies of the Royal Dutch/Shell Group under the designations "HVI", or "XHVI” (trade mark).
• the viscosity of the lubricating base oils present in the compositions according to the present invention may vary within wide ranges, and is generally from 3 to 35 mm2/s at 100°C.
• the lubricating oil compositions according to the present invention may contain various other additives, known in the art, such as viscosity index improvers, e.g. linear or star-shaped polymers of a diene such as isoprene or butadiene, or a copolymer of such a diene with optionally substituted styrene. These copolymers are suitably block copolymers and are preferably hydrogenated to such an extent as to saturate most of the olefinic unsaturation.
• Other suitable additives include dispersant V.I.
• detergents such as those based on block copolymers, or polymethacrylates, extreme pressure/anti-wear additives such as zinc or sodium dithiophosphates, ashless dispersants such as polyolefin-substituted succinimides, e.g. those described in GB-A-2 231 873, anti-oxidants, friction modifiers or metal-containing detergents such as phenates, sulphonates, alkylsalicylates or naphthenates, all of which detergents may be overbased.
• extreme pressure/anti-wear additives such as zinc or sodium dithiophosphates
• ashless dispersants such as polyolefin-substituted succinimides, e.g. those described in GB-A-2 231 873
• anti-oxidants such as phenates, sulphonates, alkylsalicylates or naphthenates, all of which detergents may be overbased.
• the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) may also be used as a dispersant additive in fuels.
• the present invention further provides a fuel composition comprising a major amount (more than 50%w) of a fuel and a minor amount (less than 50%w), preferably from 0.001 to 2%w, more preferably from 0.001 to 0.5%w and especially from 0.002 to 0.2%w (active matter), of a reaction product according to the invention, the percentages by weight being based on the total weight of the composition.
• Suitable fuels include gasoline and diesel fuel. These base fuels may comprise mixtures of saturated, olefinic and aromatic hydrocarbons. They can be derived from straight-run gasoline, synthetically produced aromatic hydrocarbon mixtures, thermally catalytically cracked hydrocarbon feedstocks, hydrocracked petroleum fractions or catalytically reformed hydrocarbons.
• the fuel compositions according to the present invention may contain various other additives known in the art such as a lead compound as anti-knock additive; antiknock additives other than lead compounds such as methyl cyclopentadienyl-manganese tricarbonyl or ortho-azidophenyl; co-antiknock additives such as benzoylacetone; dehazers (e.g.
• ethoxylated glycerols such as that commercially available as “SURDYNE” (trade mark) M155 (ex Shell Chemicals, UK) or alkoxylated phenol formaldehyde polymers such as those commercially available as “NALCO” (trade mark) 7DO7 (ex Nalco), “TOLAD” (trade mark) 2683 (ex Petrolite) or “SURDYNE” (trade mark) D265, M153, M154 or M156 (ex Shell Chemicals, UK)); anti-foaming agents (e.g.
• succinic acid derivative that commercially sold by Rhein Chemie, Mannheim, Germany as "RC 4801", or polyhydric alcohol esters of a succinic acid derivative, the succinic acid derivative having on at least one of its alpha carbon atoms an unsubstituted or substituted aliphatic hydrocarbon group containing from 20 to 500 carbon atoms, e.g. the pentaerythritol diester of polyisobutylene-substituted succinic acid); reodorants; anti-wear additives; anti-oxidants (e.g.
• phenolics such as 2,6-di-tert-butylphenol, or phenylenediamines such as N,N'-di-sec-butyl-p-phenylenediamine); metal deactivators; lubricity agents (e.g. those commercially available as EC831 (ex Paramins) or "HITEC” (trade mark) 580 (ex Ethyl Corporation)); or carrier fluids such as a polyether e.g.
• polyisobutylene having from 20 to 175, particularly 35 to 150, carbon atoms, or a polyalphaolefin having a viscosity at 100°C in the range 2 x 10 ⁇ 6 to 2 x 10 ⁇ 5 m2/s (2 to 20 centistokes), being a hydrogenated oligomer containing 18 to 80 carbon atoms derived from at least one alphaolefinic monomer containing from 8 to 18 carbon atoms.
• the lubricating oil and fuel compositions of the invention may be prepared by adding the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) separately to a lubricating oil or fuel.
• an additive concentrate is blended with the lubricating oil or fuel.
• Such a concentrate generally comprises an inert carrier fluid and one or more additives in a concentrated form.
• the present invention also provides an additive concentrate comprising an inert carrier fluid and from 10 to 80%w (active matter) of a reaction product according to the invention, the percentages by weight being based on the total weight of the concentrate.
• inert carrier fluids include hydrocarbons and mixtures of hydrocarbons with alcohols or ethers, such as methanol, ethanol, propanol, 2-butoxyethanol or methyl tert-butyl ether.
• the carrier fuid may be an aromatic hydrocarbon solvent such as toluene, xylene, mixtures thereof or mixtures of toluene or xylene with an alcohol.
• the carrier fluid may be a mineral base oil, such as those sold by member companies of the Royal Dutch/Shell Group under the designations "HVI” or "XHVI” (trade mark), e.g. "HVI 60" base oil.
• the present invention still further provides the use of a reaction product according to the invention as a dispersant additive.
• the present invention will be further understood from the following illustrative examples.
• M n the number average molecular weights specified for the polyisobutenyl moieties in the polyisobutenyl succinic anhydride/succinimide were determined by quantitative reaction with ozone, on the assumption that each oligomer chain contains one double bond, as will be readily understood by those skilled in the art.
• the number average molecular weights quoted were determined by modern gel permeation chromatography using polystyrene standards, e.g. as described in W.W. Yau, J.J. Kirkland and D.D. Bly, "Modern Size Exclusion Liquid Chromatography", John Wiley and Sons, New York, 1979.
• Active matter content was determined by separating inactive material from the desired active matter on an aluminium oxide column using diethyl ether as eluant; acid value was determined according to ASTM D 664; and Total Base Number (adjusted to 100% active matter) was determined in accordance with ASTM D 2896.
• a xylene solution 2454 g of a polyisobutenyl succinic anhydride (PIBSA; polyisobutenyl M n 2400) prepared by the process described in EP-A-0542380.
• PIBSA polyisobutenyl succinic anhydride
• the PIBSA/xylene solution contained 42.3%w xylene and 37.6%w active matter PIBSA.
• the acid value of the PIBSA (after removal of the xylene) was found to be 0.486 meq/g.)
• the mixture so formed was stirred with toluene (4.5 l) until it was homogeneous.
• a polyamine mixture (92.81 g) containing tetraethylene pentamine, pentaethylene hexamine and higher ethylene polyamines in a weight ratio of 1:2:1 (commercially available from Delamine B.V., Netherlands) was then added and the resulting composition heated to 120°C for four hours, with removal of water and tetrahydro-furan using a Dean and Stark trap.
• the polyanhydride derivatives obtained in (i) above (0.8g) were added, with stirring, to a reaction vessel containing toluene (300 ml), tetrahydrofuran (50 ml), triethylene tetramine (0.6 g, 4.1 mmol), and a polyisobutenyl succinic anhydride (22 g) (65%w active matter; polyisobutenyl M n 2400; acid value of 0.486 meq/g) prepared by the process described in EP-A-0542380.
• the reaction mixture was refluxed for an hour and a half, with removal of water using a Dean and Stark trap.
• Example 8 (ii) The procedure described in Example 8 (ii) was repeated using 0.72 g of the polyanhydride derivatives, 0.9 g pentaethylene hexamine and 19 g of the polyisobutenyl succinic anhydride. Infrared spectral analysis of the end product showed v max at 1770 cm ⁇ 1 (m) and 1700 cm ⁇ 1 (vs). The end product had an active matter of 65%, a total base number of 0.73 mg KOH/g and a nitrogen content of 1.3%w.
• Example 10 was repeated using different amounts of the polyanhydride derivatives and/or polyisobutylene succinimide as detailed in Table II below. Table II also shows the total base number and nitrogen content of the polyimide derivatives obtained. Table II Ex. No. Reagents Polyimide Derivatives Product of Example 1(i) (g) PIB Succinimide (g) Total Base Number (mg KOH/g) Nitrogen content (%w) 11 3 62.7 0.27 1.16 12 0.88 29.3 0.51 1.18 13 1.5 62.7 0.49 1.17 14 1.5 62.7 0.58 1.17 15 0.31 31 0.35 1.13
• Example 16 (ii) was repeated using different amounts of the polyanhydride derivatives, as indicated in Table III below.
• the end products also both had an active matter of 48%.
• the total base number and nitrogen content of the polyimide derivatives obtained are also shown in Table III.
• Table III Ex. No. Reagents Polyimide Derivatives Product of Example 16(i) (g) PIB Succinimide (g) Total Base Number (mg KOH/g) Nitrogen content (%w) 17 3 62.7 0.66 1.16 18 1.5 62.7 0.7 1.18
• 1,5-hexadiene (10 g, 0.122 mol) and maleic anhydride (50 g, 0.51 mol) in toluene (20 ml) were heated in a sealed autoclave at 180°C for 24 hours. Solvent and any unreacted maleic anhydride were removed under reduced pressure (140°C, 500 Pa) to give the crude double-ene, Diels-alder adduct (15 g). Infrared spectral analysis of the product showed v max at 1858 cm ⁇ 1 (s) and 1777 cm ⁇ 1 (s).
• polyimide derivatives of Examples 1 and 8 to 18 were incorporated in lubricating oils to give concentrations of 1.5%w active matter and tested for compatibility with fluoroelastomer seal materials according to the method of DIN 53504 and, specifically, Daimler Benz specification DB 6615. Percentage reduction in tensile strength (TS) and elongation at break (EB) were assessed. The test results depend upon the particular seal materials used, and therefore comparative series should be tested with seals from consistent batches. A low result indicates good performance.
• TS tensile strength
• EB elongation at break

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• 1995
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