EP0318848A2 - Huile lubrifiante contenant des polymères-bloc hydrogénés de polydioléfines - Google Patents
Huile lubrifiante contenant des polymères-bloc hydrogénés de polydioléfines Download PDFInfo
- Publication number
- EP0318848A2 EP0318848A2 EP88119638A EP88119638A EP0318848A2 EP 0318848 A2 EP0318848 A2 EP 0318848A2 EP 88119638 A EP88119638 A EP 88119638A EP 88119638 A EP88119638 A EP 88119638A EP 0318848 A2 EP0318848 A2 EP 0318848A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- block
- lubricating oil
- hydrogenated
- polybutadiene
- block polymers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/12—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing conjugated diene
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- C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
- C10M101/02—Petroleum fractions
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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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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- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
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- 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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- C10M2219/082—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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- C10M2219/00—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
- C10M2219/089—Overbased salts
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- 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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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- 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
- C10M2219/106—Thiadiazoles
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- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- 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 fueled engines
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- 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
- C10N2040/252—Diesel engines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C10N2040/253—Small diesel engines
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- 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
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- 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
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- 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 invention relates to the use of hydrogenated polydiolefin block polymers as viscosity index-improving additives for mineral lubricating oils.
- the viscosity index (VI) of mineral oil-based lubricants is conventionally set by polymer additives. It is known that the viscosity index of mineral lubricating oils can be improved by adding ethylene / butene (1) copolymers.
- DE-OS 23 58 764 describes hydrogenated polydiolefins as additives to mineral lubricating oils in which 30 to 95, preferably 40 to 65% of the double bonds have a 1,2-configuration before the hydrogenation.
- these polymers are not yet satisfactory in terms of the viscosity index-improving effect and durability in the engine.
- mineral lubricating oils which, as VI improvers, contain a hydrogenated block (co) polymer of the formal structure AB, the polymer block A - before the hydrogenation - a polybutadiene with a 1,2 content between 7 and 20%, the polymer block B - before the hydrogenation - a polybutadiene or a copolymer of butadiene and isoprene has a 1,2 content of more than 35%, or the polymer block B is a homopolymer of isoprene.
- the polymers are advantageously prepared by anionic polymerization of the monomers in the presence of a catalyst system from organolithium compounds in inert solvents. It is known that in the polymerization of butadiene in the presence of Lewis bases, block copolymers are obtained if either Lewis bases are added in the course of the polymerization, or if the polymerization is carried out in several stages, the amount being added with each addition of monomers on Lewis bases is changed (US Pat. No. 3,140,278).
- Suitable organolithium initiators are, for example, methyl lithium, ethyl lithium, n-, sec-butyllithium or isopropyllithium. N- or sec-butyllithium is preferably used.
- straight-chain and branched aliphatic hydrocarbons such as n-octane or n-hexane, and simple or substituted cycloaliphatic and aromatic hydrocarbons such as cyclohexane, methylcyclohexane, toluene, and any mixture of aliphatic, cycloaliphatic and aromatic hydrocarbons are used as solvents for the polymerization .
- Cyclohexane is preferred as the solvent.
- Suitable Lewis bases are ethers, such as diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether, or tertiary amines, such as tetramethylethylene diamine, pyridine, N-methylmorpholine or 1,2-dipiperidinoethane.
- All feed materials must be freed from oxygen and proton-active impurities; this can e.g. by contact with metal organyls or by adsorptive cleaning e.g. on alumina.
- the polymerization is carried out under inert gas conditions at temperatures from -20 to 140 ° C, preferably at 25 to 80 ° C at pressures at which the monomers and solvents do not evaporate at the polymerization temperature.
- a sufficient amount of water, methanol or isopropanol is added to the polymerization mixture in order to deactivate the active end groups or excess initiator.
- the active end groups of the polymers can also be functionalized by reaction with suitable reagents such as ethylene oxide, ethylene sulfide or Schiff bases.
- the block polymers are generally prepared in such a way that in a first stage a partial amount of the diene hydrocarbon to form the A block is completely polymerized in the inert solvent, in the second polymerization step the second partial amount of diene hydrocarbon to form the B block is completely reacted . In both polymerization stages, just as much Lewis base is added to the reaction mixture as is required for the desired 1,2-incorporation of the diene, taking into account the polymerization temperature.
- the polymers are then hydrogenated. This can be done either in a homogeneous phase using catalysts based on salts, especially carboxylates, alkoxides or enolates of cobalt, nickel or iron, which are combined with metal alkyls, especially aluminum alkyls, at temperatures from 40 to 130 ° C and hydrogen pressures from 1 to 100 bar respectively.
- catalysts based on salts especially carboxylates, alkoxides or enolates of cobalt, nickel or iron, which are combined with metal alkyls, especially aluminum alkyls, at temperatures from 40 to 130 ° C and hydrogen pressures from 1 to 100 bar respectively.
- the hydrogenation can also be carried out in a heterogeneous phase over suspended or fixedly arranged lumpy catalysts.
- nickel or platinum metals are used as catalysts at hydrogen pressures of 20 to 300 bar and temperatures between 40 and 300 ° C (e.g. according to DE-AS 1 106 961 or DE-OS 1 595 345).
- the polymerization mixture can be heated directly to dryness or treated with steam by known methods, the solvent being distilled off. It can also be precipitated with an excess of a precipitant such as ethanol, mechanically separated and dried or worked up by extruder degassing.
- a precipitant such as ethanol
- the number average molecular weight of the hydrogenated block polymer to be used according to the invention can be within a wide range, but the average molecular weight should advantageously be between 30,000 and 150,000.
- the weight ratio of blocks A and B to one another can also vary very greatly, but a ratio between 0.25 and 4 is preferred.
- the hydrogenated block polymers are dissolved in amounts of 0.5 to 6, preferably 1 to 5% by weight in the mineral oil at 80 to 130 ° C.
- Suitable mineral lubricants are conventional hydrocarbons used for lubricating oils, which are obtained from naturally occurring, paraffinic or naphthenic petroleum by distillation and subsequent refining.
- the mineral lubricating oil compositions can also contain other known additives, for example antioxidants, agents for lowering the pour point, dyes, detergents, etc.
- the diene microstructure of the polymers is determined by Fourier analysis of the infrared spectra.
- the AB block polymer has the following structure: Molecular weight A block: 44,000 g / mol Molecular weight AB block: 65,000 g / mol Microstructure A block: 8.2% (1,2-vinyl) Microstructure B block: 38% (1,2-vinyl)
- the block polymer obtained is hydrogenated by adding a catalyst solution of 1.4 g of nickel (II) acetylacetonate in 80 g of toluene, mixed with 30 ml of a 20% by weight solution of aluminum triisobutyl in hexane at a hydrogen pressure of 15 bar and 80 ° C. Hydrogenation temperature.
- the hydrogenated block polymer is precipitated by adding ethanol, isolated and dried at 60 ° C. in vacuo.
- the polymers according to Examples 1 and 2 are dissolved in a mineral oil at 115 ° C.
- the base oil has a viscosity of 41.00 mm2 / s at 37.8 ° C and a viscosity of 6.25 mm2 / s at 98.9 ° C.
- Some lubricant-related data are listed in Table 1.
- Table 1 Polymer conc. in the solution (% by weight) Viscosity at 98.9 ° C (mm2 / s) Viscosity at 37.8 ° C (mm2 / s) VI (according to DIN 51 564) example 1 1.5 15.74 83.95 201
- Example 2 1 11.34 58.92 190
- the polybutadiene obtained in this way has the following structure: Molecular weight: 38,000 g / mol Microstructure: 52% (1,2-vinyl)
- Example 2 The hydrogenation and workup is carried out analogously to Example 1. It still contains about 0.8% olefinic double bonds.
Landscapes
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873741097 DE3741097A1 (de) | 1987-12-04 | 1987-12-04 | Schmieroel, enthaltend hydrierte polydiolefinblockpolymere |
DE3741097 | 1987-12-04 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0318848A2 true EP0318848A2 (fr) | 1989-06-07 |
EP0318848A3 EP0318848A3 (en) | 1989-08-16 |
EP0318848B1 EP0318848B1 (fr) | 1991-05-08 |
Family
ID=6341866
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88119638A Expired - Lifetime EP0318848B1 (fr) | 1987-12-04 | 1988-11-25 | Huile lubrifiante contenant des polymères-bloc hydrogénés de polydioléfines |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0318848B1 (fr) |
DE (2) | DE3741097A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992016567A1 (fr) * | 1991-03-13 | 1992-10-01 | Exxon Chemical Patents Inc. | Ameliorations apportees a des polymeres modificateurs de viscosite |
WO1992016568A1 (fr) * | 1991-03-15 | 1992-10-01 | Exxon Chemical Patents Inc. | Polymeres de polybutadiene utilises comme modificateurs ameliores de viscosite |
WO1996028523A1 (fr) * | 1995-03-14 | 1996-09-19 | Exxon Chemical Patents Inc. | Additifs et compositions de fuel-oil |
EP0837921A1 (fr) * | 1995-06-07 | 1998-04-29 | Mobil Oil Corporation | Dispersants capables egalement d'ameliorer l'indice de viscosite, choisis parmi des polymeres hydrogenes selectivement |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3378877B1 (fr) | 2017-02-28 | 2019-06-19 | Evonik Oil Additives GmbH | Polybutadiènes hydrogénés utiles en tant qu'additifs de lubrification |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3312621A (en) * | 1964-09-28 | 1967-04-04 | Exxon Research Engineering Co | Lubricants having a high viscosity index |
DE2358764A1 (de) * | 1973-11-26 | 1975-06-05 | Basf Ag | Mineralschmieroeladditive |
FR2346439A1 (fr) * | 1976-04-02 | 1977-10-28 | Exxon Research Engineering Co | Copolymeres sequences en degrade hydrogenes de dienes conjugues et d'un compose vinyl aromatique convenant comme additifs pour huiles lubrifiantes |
EP0024314A1 (fr) * | 1979-08-20 | 1981-03-04 | The Firestone Tire & Rubber Company | Copolymères en blocs hydrogénés de butadiène contenant un bloc de microstructure 1,4 et un bloc de microstructure 1,2 |
-
1987
- 1987-12-04 DE DE19873741097 patent/DE3741097A1/de not_active Withdrawn
-
1988
- 1988-11-25 DE DE8888119638T patent/DE3862747D1/de not_active Expired - Lifetime
- 1988-11-25 EP EP88119638A patent/EP0318848B1/fr not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3312621A (en) * | 1964-09-28 | 1967-04-04 | Exxon Research Engineering Co | Lubricants having a high viscosity index |
DE2358764A1 (de) * | 1973-11-26 | 1975-06-05 | Basf Ag | Mineralschmieroeladditive |
FR2346439A1 (fr) * | 1976-04-02 | 1977-10-28 | Exxon Research Engineering Co | Copolymeres sequences en degrade hydrogenes de dienes conjugues et d'un compose vinyl aromatique convenant comme additifs pour huiles lubrifiantes |
EP0024314A1 (fr) * | 1979-08-20 | 1981-03-04 | The Firestone Tire & Rubber Company | Copolymères en blocs hydrogénés de butadiène contenant un bloc de microstructure 1,4 et un bloc de microstructure 1,2 |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5310490A (en) * | 1991-03-13 | 1994-05-10 | Exxon Chemical Products Inc. | Viscosity modifer polymers |
US5543469A (en) * | 1991-03-13 | 1996-08-06 | Exxon Chemical Patents Inc. | Viscosity modifier polymers |
WO1992016567A1 (fr) * | 1991-03-13 | 1992-10-01 | Exxon Chemical Patents Inc. | Ameliorations apportees a des polymeres modificateurs de viscosite |
CN1048506C (zh) * | 1991-03-13 | 2000-01-19 | 埃克森化学专利公司 | 制备改进的粘度调节剂聚合物的方法 |
US5945485A (en) * | 1991-03-15 | 1999-08-31 | Exxon Chemical Patents Inc | Viscosity modifier polybutadiene polymers |
WO1992016568A1 (fr) * | 1991-03-15 | 1992-10-01 | Exxon Chemical Patents Inc. | Polymeres de polybutadiene utilises comme modificateurs ameliores de viscosite |
US5310814A (en) * | 1991-03-15 | 1994-05-10 | Exxon Chemical Patents Inc. | Viscosity modifier polybutadiene polymers |
AU657319B2 (en) * | 1991-03-15 | 1995-03-09 | Exxon Chemical Patents Inc. | Improved viscosity modifier polybutadiene polymers |
US5703171A (en) * | 1991-03-15 | 1997-12-30 | Exxon Chemical Patents Inc | Viscosity modifier polybutadiene polymers |
CN1050142C (zh) * | 1991-03-15 | 2000-03-08 | 埃克森化学专利公司 | 制备改进的粘度调节剂聚丁二烯聚合物的方法 |
WO1996028523A1 (fr) * | 1995-03-14 | 1996-09-19 | Exxon Chemical Patents Inc. | Additifs et compositions de fuel-oil |
EP0837921A4 (fr) * | 1995-06-07 | 1998-10-07 | Mobil Oil Corp | Dispersants capables egalement d'ameliorer l'indice de viscosite, choisis parmi des polymeres hydrogenes selectivement |
EP0837921A1 (fr) * | 1995-06-07 | 1998-04-29 | Mobil Oil Corporation | Dispersants capables egalement d'ameliorer l'indice de viscosite, choisis parmi des polymeres hydrogenes selectivement |
Also Published As
Publication number | Publication date |
---|---|
DE3862747D1 (de) | 1991-06-13 |
EP0318848B1 (fr) | 1991-05-08 |
EP0318848A3 (en) | 1989-08-16 |
DE3741097A1 (de) | 1989-06-15 |
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