EP0199453A2 - Polyolefinpfropfpolymere enthaltende Kohlenwasserstoffzusammensetzungen - Google Patents

Polyolefinpfropfpolymere enthaltende Kohlenwasserstoffzusammensetzungen Download PDF

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Publication number
EP0199453A2
EP0199453A2 EP86301906A EP86301906A EP0199453A2 EP 0199453 A2 EP0199453 A2 EP 0199453A2 EP 86301906 A EP86301906 A EP 86301906A EP 86301906 A EP86301906 A EP 86301906A EP 0199453 A2 EP0199453 A2 EP 0199453A2
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European Patent Office
Prior art keywords
polymer
polymer according
monomer
functional monomer
backbone
Prior art date
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EP86301906A
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English (en)
French (fr)
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EP0199453A3 (de
Inventor
Maria Magdalena Kapuscinski
Larry Dale Grina
Ronald Edward Jones
Rodney Lu-Dai Sung
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Texaco Development Corp
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Texaco Development Corp
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Priority claimed from US06/726,567 external-priority patent/US4820776A/en
Application filed by Texaco Development Corp filed Critical Texaco Development Corp
Publication of EP0199453A2 publication Critical patent/EP0199453A2/de
Publication of EP0199453A3 publication Critical patent/EP0199453A3/de
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    • 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

Definitions

  • This invention relates to hydrocarbons including hydrocarbon fuel oils and lubricating oil. More particularly, it relates to hydrocarbons which contain graft polymers which permit attainment of improved properties.
  • hydrocarbon fuels and lubricating oils must be formulated, as by addition of various additives, to improve their properties.
  • hydrocarbon fuels typified by fuels boiling in the gasoline boiling range, kerosene, middle distillate fuels, home heating oils, etc.
  • undesirable characteristics typified by formation of solid deposits within the system.
  • This invention provides a polymer comprising an oil-soluble backbone polymer having a linear carbon chain attached to which are additional units derived from a first functional monomer having at least one atom of nitrogen, sulphur and/or oxygen in a heterocyclic ring.
  • This invention also provides a method of producing such a polymer by heating the backbone polymer and the first functional monomer with a free-radical initiator at a temperature at least as high as the decomposition temperature of the initiator.
  • this invention comprises a polymer as defined above and having additional graft units derived from a second monomer which is an amine having a polymerisable ethylene double bond.
  • This invention also provides methods of producing the polymers having units derived from the second monomer, by:
  • This invention additionally provides a lubricating oil composition containing as additive a polymer of the types defined above.
  • this invention provides a fuel oil composition containing as additive a polymer of the type comprising both types of monomer.
  • the charge polymer which may be employed according to this invention is an oil-soluble, substantially linear, carbon-carbon backbone polymer.
  • Typical carbon-carbon backbone polymers prepared from monomers bearing an ethylenically unsaturated polymerizable double bond which may be employed include homopolymers or copolymers prepared from monomers containing moieties of the skeleton wherein A may be hydrogen; monovalent hydrocarbon such as alkyl, aryl, etc.; phenyl; acyoxy, such as acetyloxy (or less preferably -COOR where R is hydrocarbon); halide, etc.; R" may be divalent hydrocarbon typified by alkylene, alkarylene, aralkylene, cycloalkylene, arylene, etc.
  • Illustrative of such monomers may be acrylates, methacrylates, vinyl halides (such as vinyl chloride), styrene, olefins such as propylene, butylene, etc., vinyl acetate; dienes such as butadiene, isoprene, hexadiene, ethylidene norbornene, etc.
  • the polymers can be homopolymers of olefins, (such as polypropylene, polybutylene, etc.) or dienes, (such as hydrogenated polyisoprene), or copolymers of ethylene with e.g.
  • butylene and higher olefins styrene with isoprene and/or butadiene may be employed.
  • the preferred carbon-carbon backbone polymers include ethylene-propylene copolymers (EPM or EPR) and ethylene-propylene-diene terpolymers (EPDM or EPT).
  • the charge polymer is an ethylene-propylene copolymer (EPM, also called EPR polymers), it may be formed by copolymerization of ethylene and propylene under known conditions, preferably Ziegler-Natta reaction conditions.
  • the preferred EPM copolymers contain units derived from ethylene in amounts of 40 to 70 mol %, preferably 50 to 60 mol %, e.g. 55 mol %, the remainder being derived from propylene.
  • the molecular weight M of the EPM copolymers which may be employed may be 10,000 to 1,000,000, preferably 20,000 to 200,000, e.g. 140,000.
  • the molecular weight distribution may be characterized by M w/ M n of less than 15, preferably 1.2 to 10, e.g. 1.6.
  • EPM copolymers which may be employed in this invention are the following, the first listed being preferred:
  • the charge polymer is an ethylene-propylene-diene terpolymer (EPT or EPDM)
  • the third monomer is commonly a non-conjugated diene typified by dicyclopentadiene; 1,4-hexadiene; or ethylidene norbornene.
  • Polymerization is effected under known conditions generally comparable to those employed in preparing the EPM products.
  • the preferred terpolymers contain units derived from ethylene in amount of 40 to 70 mol %, preferably 50 to 65 mol %, e.g. 60 mol %, and units derived from the propylene in amount of 20 to 60 mol %, preferably 30 to 50 mol %, e.g.
  • the molecular weight M of the terpolymers may typically be 10,000 to 1,000,000, preferably 20,000 to 200,000, e.g. 120,000.
  • Molecular weight distribution of the useful polymers is preferably narrow, viz a M w / M n of typically less than 15, preferably 1.5 to 10, e.g. 2.2.
  • the EPM and EPT polymers may contain minor portions (typically less than 30%) of units derived from other copolymerizable monomers.
  • units derived from the first functional monomer are bonded onto these oil-soluble, substantially linear, carbon-carbon, backbone polymers.
  • first functional monomer includes a polymerizable ethylenic double bond, (as is the case for example with the reaction product of allyl glycidyl ether and phenothiazine) bonding may be effected by graft polymerization under graft polymerization conditions.
  • bonding may be effected in the presence of a free-radical initiator catalyst.
  • the functional monomers which may be employed may be monocyclic, or polycyclic; and the nitrogen, sulphur and/or oxygen may be contained in the same or a different ring.
  • the functional monomer is polycyclic and nitrogen and sulphur are in the same heterocyclic ring.
  • the functional monomer can be a heterocyclic/ aromatic or heterocyclic compound containing sulphur, nitrogen or oxygen, or a combination thereof.
  • the compounds which may be used as the functional monomer include:
  • the preferred first functional monomer is phenothiazine, which is a three-ring compound containing nitrogen and sulphur atoms in the same ring. It is preferred to use one functional monomer although it may be possible to use more than one such functional monomer, i.e. to bond them to the polymer either simultaneously or sequentially.
  • 100 parts by weight of charge EPM or EPT may be added to 100 to 1000 parts by weight, e.g. 300 parts by weight of diluent-solvent.
  • Typical diluent-solvents are hydrocarbon solvents, such as n-hexane or n-heptane, tetrahydrofuran, or mineral oil.
  • a preferred solvent is a commercial hexane containing principally hexane isomers.
  • the reaction mixture may then be heated to a temperature of 60 to 180°C, preferably 150 to 170°C, e.g. 155°C at a pressure of 0.2 to 2.2 MPa, preferably 1.3 to 1.65 MPa, e.g. 1.5 MPa.
  • the first functional monomer typically phenothiazine
  • the first functional monomer is admitted in amount of 1 to 40 parts by weight, e.g. 2 parts by weight, as a solution in 2 to 20 parts by weight, e.g. 8 parts by weight of diluent-solvent, typically tetrahydrofuran (THF).
  • diluent-solvent typically tetrahydrofuran (THF).
  • diluent-solvent typically tetrahydrofuran (THF).
  • diluent-solvent typically tetrahydrofuran (THF).
  • diluent-solvent typically tetrahydrofuran (THF).
  • diluent-solvent typically tetrahydrofuran (THF).
  • a free radical initiator include dicumyl peroxide, di-t-butyl peroxide, benzoyl peroxide, di-isopropyl peroxide, azobisisobut
  • the reaction is carried out at a temperature at least as high as the decomposition temperature of the initiator, typically 60°C or higher.
  • Reaction is typically carried out at 60 to 180°C, e.g. 155°C and 1.3 to 1.65 MPa, e.g. 1.5 MPa, during which time bonding of the functional monomer onto the base EPM or EPT polymer occurs.
  • the product typically contains 0.1 to 60 units, e.g. 3 units, derived from functional monomer per 1000 carbon atoms of the charge backbone polymer.
  • the polymerization solvent may be exchanged with a heavier solvent, such as SUS 100 oil typified by SNO-100.
  • Product polymer is typically obtained as a solution of 4 to 20 parts by weight, e.g. 8.5 parts by weight thereof in 80 to 96 parts by weight, e.g. 91.5 parts by weight of solvent.
  • graft units derived from a second amine graft monomer are grafted on.
  • the second monomer which may be grafted onto the backbone polymer according to one embodiment of this invention may have the formula wherein R is a hydrocarbon group having a polymerizable ethylenic double bond, and R' and R", which may be the same or different, are each hydrogen, a hydrocarbon group, or a hydrocarbon group with an oxygen, sulphur or nitrogen atom, or R' and R" together with the nitrogen atom to which they are attached constitute a heterocyclic ring.
  • R' and R" may be hydrogen or a hydrocarbon including alkyl, alkaryl, aralkyl, cycloalkyl, and aryl.
  • the group -NR'R" may represent a heterocyclic ring as in the preferred N-vinyl pyrrolidone; 1-vinyl imidazole; or 4-vinyl pyridine.
  • R' and R" may be a hydrogen or a hydrocarbon moiety containing one or more nitrogen, sulphur or oxygen atoms.
  • Illustrative amines which may be employed include N-vinylpyrrolidone, 1-vinylimidazole, 4-vinylpyridine, and allylamine; N-vinylpyrrolidone being preferred.
  • the second monomer may alternatively be a more complex amine reaction product, formed by the reaction of an amine, typified by morpholine or N-methyl piperazine, and an epoxy compound typified by allyl glycidyl ether. It may be a monomer formed for example from the reaction of crotonaldehyde and N-(3-aminopropyl) morpholine.
  • the temperatures, pressures, solvents, initiators, etc. used to graft on the second monomer may be generally the same as those used to add the first monomer to the backbone polymer, and so will not be repeated here.
  • the second (amine) monomer is preferably grafted on to the backbone polymer before the first monomer.
  • the second monomer typically N-vinyl-pyrrolidone
  • a hydrocarbon solution of the initiator are added to a solution of the backbone polymer, preferably in the sane solvent.
  • the initiator may be added in an amount of 0.2 to 10 parts by weight, e.g. 2 parts by weight in 0.8 to 40 parts by weight, e.g. 16 parts by weight of solvent.
  • the reaction is carried out at a temperature at least as high as the decomposition temperature of the initiator, typically 60°C or higher.
  • Reaction is typically carried out at 60 to 180°C, e.g. 155°C, and 1.3 to 1.65 MPa, e.g. 1.5 MPa during which time graft polymerization of the amine onto the backbone polymer occurs.
  • the final product graft polymer may be typically characterized by the presence of the following typical units: in which n is at least 1. Typically there may be 0.1 to 80, e.g. 6 amine units per 1000 carbon atoms in the polymer backbone.
  • R"' is a saturated divalent group corresponding to the group R in the amine monomer.
  • the first monomer is subsequently reacted with the resulting polymer having grafted amine units.
  • the first monomer has already been fully defined above, and is incorporated in the same way as before.
  • the first monomer typically phenothiazine
  • the first monomer is admitted in an amount of 1 to 40 parts by weight, e.g. 4 parts by weight, as a solution in 1 to 40 parts by weight, e.g. 16 parts by weight, of diluent-solvent-typically tetrahydrofuran (THF).
  • THF diluent-solvent-typically tetrahydrofuran
  • the preferred amount in this embodiment is 0.2 to 40 parts by weight, e.g. 2 parts by weight of initiator in 0.8 to 40 parts by weight, e.g. 6 parts by weight of solvent hexane.
  • Temperature and pressure conditions are generally in the same ranges as already defined.
  • the polymerization solvent may be exchanged with a heavier solvent, such as SUS 100 oil.
  • Product graft polymer is typically obtained as a solution of 4 to 20 parts by weight, e.g. 8.5 parts by weight thereof in 80 to 96 parts by weight, e.g. 91.5 parts by weight of solvent.
  • the product so formed in this embodiment of the invention may be an oil-soluble, substantially linear, carbon-carbon backbone polymer of molecular weight M of 10,000 to 1,000,000, preferably 20,000 to 200,000, e.g. 140,000, bearing thereon (per 1,000 carbon atoms in the polymer backbone) 0.1 to 80 units, preferably 1 to 15 units, e.g. 6 units of second graft monomer, and 0.1 to 60 units, preferably 1 to 12 units, e.g. 3 units of first monomer.
  • the polymers prepared with both types of monomer may find use in middle distillate fuel oils as dispersants when present in effective amount of 0.001 to 2 weight %, e.g. 0.5 weight %.
  • Typical fuel oils may include middle distillate fuel oils including kerosene, home heating oils, diesel fuel, etc.
  • the polymer prepared from either embodiment may find use in lubricating oils as multifunctional additives (e.g. dispersant, viscosity index improvers which provide anti-oxidant properties, etc.) when present in effective amount of 0.2 to 5 weight %, preferably 0.4 to 3 weight %, e.g. 0.9 weight %.
  • multifunctional additives e.g. dispersant, viscosity index improvers which provide anti-oxidant properties, etc.
  • Lubricating oils in which the dispersant viscosity index improvers of this invention may find use may include automotive, aircraft, marine, railway, etc. oils; oils used in spark ignition or compression ignition; summer or winter oils; etc.
  • the lubricating oils may be characterized by an initial boiling point (ibp) of 300 to 350°C, e.g. 320°C, an end point (ep) of 400 to 650°C, e.g. 555°C, and a density of 0.870 to 0.905 g/cm 3 , e.g. 0.882 g/cm 3 .
  • a typical lubricating oil in which the polymer of this invention may be present may be a standard SAE 5W-30 hydrocarbon motor oil formulation having the following composition:
  • the novel polymers are also characterized as anti-oxidants as determined by the Bench Oxidation Test.
  • a solution (8.5 weight %) of test polymer in SNO-100 oil is diluted with SNO-130 to give a 1.5 weight % solution of the test polymer.
  • the solution is heated with stirring and air agitation.
  • Samples are withdrawn periodically for analysis by Differential Infrared Absorption (DIR) to observe changes in the intensity of the carbonyl vibration band at 1710 em -I . Higher carbonyl vibration band intensity indicates a lower thermal-oxidative stability of the sample.
  • DIR Differential Infrared Absorption
  • Dispersancy is determined by the Bench VC Test (BVCT).
  • BVCT Bench VC Test
  • the turbidity of an oil containing an additive is measured after heating the test oil to which has been added a standard blow-by.
  • the result correlates with dispersancy is compared to three reference standards (Excellent, Good, and Fair) tested simultaneously with the test sample.
  • the numerical rating decreases with an increase in dispersant effectiveness. Results similar to or lower than that of the Good reference indicate that the additive is a good dispersant.
  • the second graft monomer i.e. the amine used in practice of this invention provides improved dispersant properties to the base polymer (which provides viscosity index improvement); and the first functional monomer provides improved anti-oxidant properties.
  • product polymers which serve as multifunctional additives (dispersants, anti-oxidants, viscosity index improvers) when added to a hydrocarbon lubricating oil or to a synthetic type lubricating oil.
  • the so-prepared graft polymers may find use in lubricating oils as dispersant anti-oxidant, viscosity index improvers when present in effective amount of O.2 to 5 weight %, preferably 0.4 to 3 weight %, e.g. 0.9 weight %.
  • the novel polymers may also be characterized as deposit protection agents as measured by the Single Cylinder CEC MWM-B Diesel Engine Test (DIN 51361 Parts I, II and IV). In this test, a solution (8.5 weight %) of polymer in SNO-100 oil is blended into a fully formulated oil which does not contain a VI improver. Results are presented in "Merits", a higher merit evidencing better protection against deposits.
  • the polymer products of this invention may be used in middle distillate fuel oils to permit attainment of improved storage stability as measured by the Potential Deposit Test (PDT) - ASTM Test D-2274.
  • PDT Potential Deposit Test
  • a rating of 1 or 2 is good; and a rating of 3 or 4 is unsatisfactory.
  • compositions of this invention it is possible by use of the compositions of this invention to improve the PDT rating of a charge diesel fuel from 4+ to a satisfactory rating of 1 by use of only 7 0 g/m of active ingredient.
  • the additives When used in fuels, the additives may be present in amount of 0.5 to 750 g/m 3 , preferably 25 to 300 g/m 3 , e.g. 70 g/m 3 .
  • the charge EPM polymer is the Epsyn polymer of molecular weight M n of 140,000, of M w/ M n ratio of 1.6, and containing 60 mol % of units derived from ethylene and 40 mol % of units derived from propylene. 100 parts of this polymer are dissolved in 300 parts of commercial hexane and added to a reaction vessel.
  • the reaction vessel is purged with nitrogen and heated to 155°C at 1.48 MPa.
  • Phenothiazine (2 parts) dissolved in 8 parts of tetrahydrofuran is added, followed by a solution of 1 part of dicumyl peroxide in 3 parts of commercial hexane.
  • the mixture is stirred at 155°C and 1.48 MPa for 1 hour.
  • Solvent Neutral Oil SNO-100 (SUS 100) (1076 parts) is then added; and the hexane is distilled off at 90 to 120°C.
  • the resulting solution contains about 8.5 % of polymer.
  • Example 1 The process of Example 1 is carried out using the following charge polymers:
  • Example 2 100 parts of the same charge EPM copolymer as used in Example 1 is mixed with 1076 parts of SNO-100 oil at 80 to 90°C and the mixture is agitated under nitrogen for 24 hours. There is then added phenothiazine (2 parts) dissolved in 8 parts of tetrahydrofuran; and the mixture is maintained at 80 to 90°C for one hour.
  • Example 5 * the procedure of Example 5 * is followed except that the phenothiazine in tetrahydrofuran is not added.
  • Example 2 the procedure of Example 1 is followed except that the polymer is EPDM containing 64 mol % of units derived from ethylene, 35 mol % of units derived from propylene, and 1 mol % of units derived from 1,4-hexadiene and having a M of 75,000 and a of 2.
  • the polymer is EPDM containing 64 mol % of units derived from ethylene, 35 mol % of units derived from propylene, and 1 mol % of units derived from 1,4-hexadiene and having a M of 75,000 and a of 2.
  • Example 6 * the procedure of Example 6 * is followed, except that the polymer employed is the same polymer as employed in Example 7.
  • Example 2 the procedure of Example 1 is followed, except that the functional monomer is (instead of phenothiazine) a monomer prepared by heating for one hour at 100 to 120°C, a mixture of equimolar amounts of allyl glycidyl ether and phenothiazine.
  • the functional monomer is (instead of phenothiazine) a monomer prepared by heating for one hour at 100 to 120°C, a mixture of equimolar amounts of allyl glycidyl ether and phenothiazine.
  • BOT Bench Oxidation Test
  • SNO-100 oil an 8.5% solution of the test polymer in SNO-100 oil is diluted with SNO-130 oil to give a 1.5% solution of the test polymer. This solution is heated with stirring and air agitation. Samples are withdrawn periodically and analyzed by (i) Differential Infrared Absorption (DIR) to observe changes in the intensity of the carbonyl vibration band at 1710 cm -1 , (ii) the Visual Clarity Test and (iii) the Lumetron Turbidity Test.
  • DIR Differential Infrared Absorption
  • the Oxidation Index is reported as the Carbonyl Group Absorbance in the Differential Infrared Spectra after 1 44 hours of oxidation.
  • the Oxidation Index may range from O up to 100 and a low rating is desired. The results below 4 are considered excellent.
  • Example 1 and 5 to 9 The clarity of the products of Example 1 and 5 to 9 is also reported visually and by the Lumetron Turbidity Test after 144 hours of oxidation.
  • the turbidity of the product is determined by a Lumetron Photoelectric Colorimeter.
  • Lumetron Turbidity is reported on a scale of 0 to 100. A rating of below 20 is satisfactory; higher ratings are less satisfactory.
  • Example 1 The product of Example 1 is also subjected to the standard CEC MWM-B Diesel Engine Test (DIN 51361 Parts I, II and IV).
  • Example 10 the product of Example 1, containing the functionalized EPM, is tested as a viscosity index improver in a conventional mineral lubricating oil at concentration of 11.5% (corresponding to 1% of grafted EPM); and in control Example 11 * , a formulation containing 11.5% of commercial non-dispersant VI improver (corresponding to 1% active ingredient) in the same system is tested.
  • Thickening Power is calculated by subtracting the viscosity of the Base Blend (4.8 cSt @ 100°C) from that of the test specimen measured at 100°C. This number (e.g. 9.89-4.8 or 5.09 in the case of Example 10) is the Thickening Power at 100°C.
  • Example 1 which describes the best mode presently known of carrying out the embodiment using both types of monomer
  • 100 parts of the polymer used in Example 1 dissolved in 300 parts of commercial hexane are added to a reaction vessel.
  • the mixture is heated to 155°C with agitation under nitrogen atmosphere at 1.48 MPa.
  • N-vinyl pyrrolidone (5 parts dissolved in 15 parts of hexane) is added followed by 5 parts of 25% dicumyl peroxide in hexane.
  • the reaction mixture is stirred for one hour.
  • phenothiazine (4 parts) dissolved in 16 parts of tetrahydrofuran is added, followed by a solution of 2 parts of dicumyl peroxide in 6 parts of commercial hexane.
  • the mixture is stirred at 155 o C and 1.48 MPa for 1 hour.
  • Solvent Neutral Oil (SUS 100) (1076 parts) is then added; and the hexane is distilled off at 90 to 120°C.
  • the resulting solution contains about 8.5% polymer.
  • the product polymer contains (per 1000 carbon atoms of polymer backbone) about 6 units derived from N-vinyl pyrrolidone and 3 units derived from phenothiazine.
  • Example 12 The process of Example 12 is repeated using the respective charge polymers used in Examples 2 to 4.
  • N-vinylpyrrolidone grafted EPM (as a 25% solution in hexane) is prepared as in Example 12.
  • Solvent hexane is exchanged for SNO-100 oil (1076 parts) to give a solution containing 8.5% of polymer.
  • This mixture contains the same quantity of N-vinyl pyrrolidone and of phenothiazine as does the product of Example 12, but in this Example 16 * , the phenothiazine is merely admixed.
  • Example 16 * the procedure of Example 16 * is followed, except that the phenothiazine in tetrahydrofuran is not added.
  • Example 12 the procedure of Example 12 is followed, except that the first graft monomer is (instead of N-vinylpyrrolidone) a monomer (8 parts) prepared by heating, for one hour at 100 to 120°C, a mixture of equimolar amounts of allyl glycidyl ether and morpholine.
  • the polymer product contains (per 1000 carbon atoms in the polymer backbone) 5 units derived from the reaction product of allyl glycidyl ether and morpholine, and 3 units derived from phenothiazine. It is recovered as a 8.5% solution in SNO-100 oil.
  • Example 16 * the procedure of Example 16 * is followed, except that the first graft monomer is the reaction product of allyl glycidyl ether and morpholine, prepared as in Example 18.
  • Example 17 * the procedure of Example 17 * is followed, except that the first graft monomer is the reaction product of allyl glycidyl ether and morpholine - prepared as in Example 18.
  • Example 12 the procedure of Example 12 is followed, except that the first functional monomer is (instead of N-vinyl pyrrolidone) a monomer (6 parts) prepared by heating for one hour at 100 to 120°C, a mixture of equimolar amounts of allyl glycidyl ether and N-methylpiperazine.
  • the polymer product contains (per 1000 carbons of polymeric chain) 4 units derived from the reaction product of allyl glycidyl ether and N-methyl piperazine and 3 units derived from phenothiazine. It is recovered as a 8.5% polymer solution in SNO-100 oil.
  • Example 12 the procedure of Example 12 is followed, except that the first functional monomer is (instead of N-vinyl pyrrolidone) a monomer (8 parts) prepared by heating for one hour at 90 to 100°C, a mixture of equimolar amounts of crotonaldehyde and N-(3-aminopropyl)morpholine.
  • the polymer product contains (per 1000 carbons of polymeric chain) 4.5 units derived from the reaction product of crotonaldehyde and N-(3-aminopropyl)morpholine, and 3 units derived from phenothiazine. It is recovered as a 8.5% solution in SNO-100 oil.
  • Example 2 100 parts of the polymer used in Example 1 are dissolved in 300 parts of commercial hexane and added to a reaction vessel. The mixture is heated to 155°C with agitation under nitrogen at 1.48 MPa. There are added (i) 5 parts of N-vinylpyrrolidone, dissolved in 15 parts of hexane, (ii) 2 parts of phenothiazine, dissolved in 8 parts of tetrahydrofuran, and (iii) 6.0 parts of dicumyl peroxide dissolved in 18 parts of hexane.
  • the product polymer contains (per 1000 carbon atoms in the polymer backbone) about 6 units derived from N-vinyl pyrrolidone and 1.5 units derived from phenothiazine.
  • Each of the products of Examples 12 and 16 * to 23 is formulated with a fully formulated base blend to yield a composition containing 0.85% of polymer; and these compositions are subjected to the Bench VC Test (BVCT).
  • BVCT Bench VC Test
  • the fully formulated base blend contains the following components: This oil has the following properties:
  • Examples 12 and 16 * to 23 are subjected to the Bench Oxidation Test to determine whether the additive is a satisfactory anti-oxidant. They are also tested in the Clarity Test and the Lumetron Turbidity Test.
  • Example 24 * there is added to the base fuel of Example 24 * , 8.5% of the polymer of Example 12 to yield a mix containing 0.01% (nitrogen content of 0.054%).
  • the modified diesel fuel is found to have a PD T rating of 1 which is satisfactory.
  • Example 26 * the procedure of Example 26 * is followed, except that the product of Example 12 is added in Example 27 and the product of Example 21 is added in Example 28 (instead of the commercial olefin copolymer dispersant VI improver) to a formulated oil not containing a VI improver.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Graft Or Block Polymers (AREA)
EP86301906A 1985-04-24 1986-03-17 Polyolefinpfropfpolymere enthaltende Kohlenwasserstoffzusammensetzungen Withdrawn EP0199453A3 (de)

Applications Claiming Priority (4)

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US726567 1985-04-24
US06/726,567 US4820776A (en) 1985-04-24 1985-04-24 Hydrocarbon compositions containing polyolefin graft polymers having amine and phenothiazine grafted moieties
US72854585A 1985-04-29 1985-04-29
US728545 1985-04-29

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WO1988008008A3 (en) * 1987-04-08 1989-01-12 Exxon Chemical Patents Inc Composition comprising nitrogen-containing hydrocarbon adducts
EP0201164A3 (en) * 1985-04-29 1989-01-18 Texaco Development Corporation Polyolefin graft polymers and lubricating compositions containing them
EP0256547A3 (de) * 1986-08-20 1989-03-01 Texaco Development Corporation Dispergierender-antioxidierender multifunktioneller Viskositätsindexverbesserer
EP0302239A3 (de) * 1987-08-03 1989-04-26 Texaco Development Corporation Zusätze für die Kontrolle des Diesel-Schnierölverbrauchs
EP0314845A1 (de) * 1984-08-20 1989-05-10 Texaco Development Corporation Öl mit Olefincopolymer als Viskositätsindexverbesserer
EP0363501A1 (de) * 1987-04-10 1990-04-18 Texaco Development Corporation Schmieröl, das eine Mannichbase enthält
EP0284234A3 (de) * 1987-03-23 1990-08-29 Texaco Development Corporation Multifunktionellen Viskositätsindexverbesserer
EP0384998A1 (de) * 1987-08-12 1990-09-05 Texaco Development Corporation Viskositätsindexverbesserer enthaltendes Schmieröl
EP0510991A1 (de) * 1991-04-24 1992-10-28 Texaco Development Corporation Multifunktioneller Viskositätsindexverbesserer
EP0515152A1 (de) * 1991-05-22 1992-11-25 Texaco Development Corporation Dispergiermittelzusatz und diese enthaltende Schmierölzusammensetzung
US5298565A (en) * 1989-04-05 1994-03-29 The Lubrizol Corporation Graft copolymers and lubricants containing such as dispersant-viscosity improvers
US5523008A (en) * 1994-10-21 1996-06-04 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
US5663126A (en) * 1994-10-21 1997-09-02 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
WO1997032946A1 (en) * 1996-03-08 1997-09-12 Dupont Dow Elastomers L.L.C. Substantially linear ethylene/alpha-olefin polymers as viscosity index improvers or gelling agents
EP0672692A3 (de) * 1989-04-18 1998-01-14 Rohm And Haas Company Hybrid-Copolymere aus stickstoffhaltigen Pfropfcopolymeren und statistischen stickstoffhaltigen Copolymeren und deren Verfahren zur Herstellung
WO1998033828A1 (en) * 1997-02-03 1998-08-06 Uniroyal Chemical Company, Inc. Lubricants containing ashless antiwear-dispersant additive having viscosity index improver credit
US6083888A (en) * 1997-09-16 2000-07-04 Shell Oil Company Dispersant viscosity index improvers
US7175678B2 (en) 2002-09-27 2007-02-13 Innospec Limited Fuel composition
CN113563530A (zh) * 2020-04-29 2021-10-29 中国石油化工股份有限公司 一种聚丙烯接枝杂环的改性材料及其制备方法与应用
CN113950494A (zh) * 2019-06-11 2022-01-18 米其林集团总公司 带有侧链咪唑官能团的接枝聚合物

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Cited By (24)

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EP0314845A1 (de) * 1984-08-20 1989-05-10 Texaco Development Corporation Öl mit Olefincopolymer als Viskositätsindexverbesserer
EP0201164A3 (en) * 1985-04-29 1989-01-18 Texaco Development Corporation Polyolefin graft polymers and lubricating compositions containing them
EP0256547A3 (de) * 1986-08-20 1989-03-01 Texaco Development Corporation Dispergierender-antioxidierender multifunktioneller Viskositätsindexverbesserer
EP0284234A3 (de) * 1987-03-23 1990-08-29 Texaco Development Corporation Multifunktionellen Viskositätsindexverbesserer
WO1988008008A3 (en) * 1987-04-08 1989-01-12 Exxon Chemical Patents Inc Composition comprising nitrogen-containing hydrocarbon adducts
EP0363501A1 (de) * 1987-04-10 1990-04-18 Texaco Development Corporation Schmieröl, das eine Mannichbase enthält
EP0302239A3 (de) * 1987-08-03 1989-04-26 Texaco Development Corporation Zusätze für die Kontrolle des Diesel-Schnierölverbrauchs
EP0384998A1 (de) * 1987-08-12 1990-09-05 Texaco Development Corporation Viskositätsindexverbesserer enthaltendes Schmieröl
US5298565A (en) * 1989-04-05 1994-03-29 The Lubrizol Corporation Graft copolymers and lubricants containing such as dispersant-viscosity improvers
EP0672692A3 (de) * 1989-04-18 1998-01-14 Rohm And Haas Company Hybrid-Copolymere aus stickstoffhaltigen Pfropfcopolymeren und statistischen stickstoffhaltigen Copolymeren und deren Verfahren zur Herstellung
EP0510991A1 (de) * 1991-04-24 1992-10-28 Texaco Development Corporation Multifunktioneller Viskositätsindexverbesserer
EP0515152A1 (de) * 1991-05-22 1992-11-25 Texaco Development Corporation Dispergiermittelzusatz und diese enthaltende Schmierölzusammensetzung
US5663126A (en) * 1994-10-21 1997-09-02 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
US5523008A (en) * 1994-10-21 1996-06-04 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
US5874389A (en) * 1994-10-21 1999-02-23 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
GB2308124B (en) * 1994-10-21 1999-03-31 Castrol Ltd Polar grafted polyolefins,methods for their manufacture,and lubricating oil co positions containing them
US6686321B2 (en) 1994-10-21 2004-02-03 Castrol Limited Polar grafted polyolefins, methods for their manufacture, and lubricating oil compositions containing them
WO1997032946A1 (en) * 1996-03-08 1997-09-12 Dupont Dow Elastomers L.L.C. Substantially linear ethylene/alpha-olefin polymers as viscosity index improvers or gelling agents
WO1998033828A1 (en) * 1997-02-03 1998-08-06 Uniroyal Chemical Company, Inc. Lubricants containing ashless antiwear-dispersant additive having viscosity index improver credit
US6083888A (en) * 1997-09-16 2000-07-04 Shell Oil Company Dispersant viscosity index improvers
US7175678B2 (en) 2002-09-27 2007-02-13 Innospec Limited Fuel composition
CN113950494A (zh) * 2019-06-11 2022-01-18 米其林集团总公司 带有侧链咪唑官能团的接枝聚合物
CN113950494B (zh) * 2019-06-11 2023-09-19 米其林集团总公司 带有侧链咪唑官能团的接枝聚合物
CN113563530A (zh) * 2020-04-29 2021-10-29 中国石油化工股份有限公司 一种聚丙烯接枝杂环的改性材料及其制备方法与应用

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EP0199453A3 (de) 1988-04-13
AU596097B2 (en) 1990-04-26
AU5630186A (en) 1986-10-30
BR8601800A (pt) 1986-12-23

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