US3869396A - Lubricating oil compositions - Google Patents
Lubricating oil compositions Download PDFInfo
- Publication number
- US3869396A US3869396A US248261A US24826172A US3869396A US 3869396 A US3869396 A US 3869396A US 248261 A US248261 A US 248261A US 24826172 A US24826172 A US 24826172A US 3869396 A US3869396 A US 3869396A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- alkyl
- oil
- lubricating oil
- methacrylates
- 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.)
- Expired - Lifetime
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- 239000010687 lubricating oil Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims abstract description 23
- -1 alkyl methacrylates Chemical class 0.000 claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 40
- 230000000994 depressogenic effect Effects 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- 239000002199 base oil Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UZMNPEQMXYMHTH-WUXMJOGZSA-N [(E)-3-(hydroxymethyl)-4-(4-methylphenyl)but-2-enyl] phosphono hydrogen phosphate Chemical compound Cc1ccc(C\C(CO)=C/COP(O)(=O)OP(O)(O)=O)cc1 UZMNPEQMXYMHTH-WUXMJOGZSA-N 0.000 description 9
- 239000001993 wax Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- JWXHIZDIJHFSIP-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(C(F)(F)F)=CC=C2N=C1C(O)=O JWXHIZDIJHFSIP-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 238000004517 catalytic hydrocracking Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229940042472 mineral oil Drugs 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 2
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
Classifications
-
- 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
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—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
- C10M145/12—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 monocarboxylic
- C10M145/14—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- 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
-
- 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
- ABSTRACT Pour points of lubricating oils are depressed by adding thereto small amounts of oil-soluble copolymer of polyalkyl methacrylates having (a) a molar percentage of alkyl methacrylates with branched alkyl chains from 5 to 25 percent, (b) at least six alkyl chains with a different number of carbon atoms, and (c) a number average molecular weight of 2,000 to 2,000,000, wherein the alkyl groups in said alkyl methacrylates contain 9 to 18 carbon atoms with an average of from 12.4 to l3.7 carbon atoms.
- lubricating oil as used in this specification also includes lubricating oil compositions which comprise, besides a lubricating oil proper, additives which render improved properties to that lubricating oil) at different temperatures is considered a measure of the suitability for application of that lubricating oil.
- lubricating oils were, until recently with relation to their viscosity properties, valued and classified according to their viscosity at 210F (99C) and 100F (38C).
- the viscosity at F (18C) is determined with a standardized method (ASTM method D 2602) and in general the requirement set is that the viscosity determined in that way be for, e.g., a W oil at most 24 Stokes.
- Base oils for the preparation of lubricating oils can be prepared from vacuum distillation fractions or residues of the vacuum distillation of crude mineral oils.
- the vacuum distillation fractions and the deasphalted residue (or mixtures of one or more of the vacuum distillation fractions and/or the residue) are treated with a solvent, e.g., sulphur dioxide, furfural and phenol, for the removal of aromatic compounds.
- a solvent e.g., sulphur dioxide, furfural and phenol
- Base oils for the preparation of lubricating oils can also be prepared by hydrocracking, which is understood to be a treatment of a mineral oil-based material with hydrogen at elevated temperature and pressure in the presence of a bifunctional catalyst comprising a metal-containing hydrogenating component on a carrier possessing cracking activity, with the object of, inter alia, increasing the viscosity index (as determined according to ASTM method D-2270) of the mineraloil-based material; deasphalted residual fractions of the vacuum distillation of a crude mineral oil are very suitable to be hydrocracked.
- hydrocracking is understood to be a treatment of a mineral oil-based material with hydrogen at elevated temperature and pressure in the presence of a bifunctional catalyst comprising a metal-containing hydrogenating component on a carrier possessing cracking activity, with the object of, inter alia, increasing the viscosity index (as determined according to ASTM method D-2270) of the mineraloil-based material; deasphalted residual fractions of the vacuum distillation of a crude mineral oil are very
- the base oils for the preparation of lubricating oils may contain considerable quantities of wax. This wax separates if the base oil for the preparation of a lubricating oil is cooled below a certain temperature. As cooling proceeds, more wax is separated until the mixture of wax and oil almost or entirely ceases to flow. The lowest temperature observed in a standard laboratory test at which the waxy mixture still flows is called the pour point. The pour point of a lubricating oil is of great practical importance. To prevent difficulties in the use of the lubricating oils their pour points should lie below the minimum temperature at which the oil is stored, transported and used.
- Dewaxing may be carried out with the aid of urea; in most cases dewaxing comprises diluting the waxy base oil for the preparation of a lubricating oil with a suitable solvent, cooling the mixture and filtering off the wax precipitated.
- the mixture is cooled to such a temperature that the dewaxed lubricating oil obtained after removal of the solvent has a pour point of about 16F (9C).
- pour-point depressants such as viscosity-index improvers, detergent additives, antioxidants, extreme-pressure additives
- a class of novel compounds of particular structure and composition has now been found which effect a great reduction in pour point not only of lubricating oils the base oil of which has been dewaxed to a pour point of that lubricating oil of about 16F, but also of lubricating oils in the preparation of which the dewaxing of the waxy base oil has been carried out in such a way that the pour point of the lubricating oil obtained is about 0F.
- These compounds are oil-soluble po1yalkyl methacrylates wherein the alkyl group has from 9-18 carbon atoms and meets the following requirements (a) the average number of carbon atoms of the alkyl chains in the methacrylates is from 12.4 to 13.7, (b) the molar percentage of the alkyl methacrylates with branched alkyl chains is from 5 to 25 percent, and (c) there are present among the alkyl chains in the methacrylates at least six alkyl chains with a different number of carbon atoms.
- Alkyl chains are considered to be present in the oilsoluble polyalkyl methacrylates if the number of those alkyl chains is at least 1 percent of the total number of alkyl chains of 9-18 carbon atoms present in the polyalkyl methacrylates. Preference is given to polyalkyl methacrylates in which the average number of carbon atoms in the alkyl chains is from 12.8 to 13.5. Oilsoluble polyalkyl methacrylates in which some of the alkyl chains contain nine carbon atoms are very suitable; polyalkyl methacrylates wherein the number of alkyl chains of nine carbon atoms is from 2 to 10 percent of the total number of alkyl chains are in particular preferred.
- the polyalkyl methacrylates according to the invention must have at least six, and preferably at least eight, alkyl chains with a different number of carbon atoms present among the alkyl chains containing 9-18 carbon atoms.
- polyalkyl methacrylates may have some alkyl chains which contain fewer than nine (e.g., l, 2 or 4) carbon atoms and/or more than 18 (e.g., 20,22) carbon atoms, it is preferred that all alkyl chains present in the polyalkyl methacrylates of the invention contain from 9-18 carbon atoms.
- polyalkyl methacrylates of the invention containing alkyl chains of 9-18 carbon atoms, at least 5 to 25 percent of which alkyl chains are branched alkyl chains.
- branched alkyl chains denotes alkyl chains which contain at least one tertiary or quaternary carbon atom.
- Polyalkyl methacrylates in which 5-15 percent of the alkyl chains are branched are particularly preferred.
- the novel polyalkyl methacrylates are obtained by polymerization, e.g., radical polymerization, of a mixture of alkyl methacrylates at least part of which consists of alkyl methacrylates with 9-18 carbon atoms in the alkyl group.
- polymerization e.g., radical polymerization
- a simple process yields polymers meeting the three aforementioned criteria.
- Very suitable polyalkyl methacrylates are prepared by polymerization of a mixture of alkyl methacrylates part of which are derived from unbranched natural and/or synthetic alcohols with 16 and/or 18 carbon atoms and the remaining part from a mixture of branched and unbranched synthetic alcohols with 9-15 carbon atoms.
- the latter alcohol mixture can be obtained, for example, by the 0x0 process or by reacting a mixture of olefins with 8-14 carbon atoms (or several mixtures of olefins in this range, e.g., a mixture of olefins with 8-10 carbon atoms and a mixture of olefins with 1 1-14 carbon atoms), with carbon monoxide and hydrogen in the presence of a complex catalyst consisting of cobalt, carbon monoxide and a phosphorus compound.
- a complex catalyst consisting of cobalt, carbon monoxide and a phosphorus compound.
- the molecular weight of the polymers of the invention can vary within wide limits. Polymers used as lubricating oil additives should have a number average molecular weight of between 2,000 and 2,000,000, in particular between 5,000 and 500,000. The molecular weight was determined by an ebullioscopic method.
- polyalkyl methacrylates When used as additives for lubricating oils they can be added directly to the oil or in the form of a concentrate obtained by mixing the polymers with a small quantity of oil.
- the concentration in which the polyalkyl methacrylates can be used may also vary within wide limits, dependent on the structure and the molecular weight of the polymer to be used, the nature and the quantity of the waxes present in the lubricating oil and the pourpoint depressing effect to be achieved. In some cases a quantity of0.01 percent w calculated on the lubricating oil composition is sufficient to reach the desired pour point. In most cases a quantity of 2.0 percent w is ample. One preferably incorporates 0.05 to 0.5 percent w of the polymers in the lubricating oil. If the application of the polymers in question is directed to V1 improvement as well as to pour-point depression it may be desirable to incorporate quantities of the polymers greater than the afore-mentioned 2.0 percent w.
- the lubricating oil compositions so obtained may also comprise other additives such as antioxidants, additives with a detergent action, viscosityincreasing compounds, anti-corrosives, anti-foaming agents, agents to improve the lubricating effect and other compounds which are usually added to lubricating oils.
- additives such as antioxidants, additives with a detergent action, viscosityincreasing compounds, anti-corrosives, anti-foaming agents, agents to improve the lubricating effect and other compounds which are usually added to lubricating oils.
- Base Oils Oil A A lubricating oil with a viscosity of 4.87 cS at 99C (210F) and 29.6 cS at 38C (100F) obtained from a Middle East crude by distillation and extraction of aromatic compounds, followed by solvent dewaxing to a pour point of 18C (0F).
- Oil B A lubricating oil with a viscosity of 4.36 cS at 99C (210F) and 23.7 cS at 38C (100F) obtained from a Middle East crude as described for oil A, dewaxed to a pour point of 24C (1 1F).
- Oil C A lubricating oil with a viscosity of 7.03 cS at 99C (210F) and 44.30 cS at 38C (100F) prepared from a deasphalted distillation residue of a Middle East crude by hydrocracking. The oil was dewaxed to a pour point of 18C (0F).
- Oil D A lubricating oil with a viscosity of 9.41 05 at 99C (210F) and 26.7 cS'at 38C (100F) pre pared from a deasphalted distillation residue of a Middle East crude by hydrocracking. The oil was dewaxed to a pour point of 18C (0F).
- Oil E A lubricating oil with a viscosity of 1 1.87 cS at 99C (210F) and 113.5 cS at 38C (100F) obtained from a Middle East crude by blending of solvent-extracted distillate fractions and a solventextracted deasphalted residue. The oil was dewaxed to a pour point of 9C (16F).
- Oil F A lubricating oil with a viscosity of 10.18 cS at 99C (210F) and 78.92 cS at 38C (100F) obtained by hydrocracking of a deasphalted distillation residue of a Middle East crude. The oil was de waxed to a pour point of 21C (-6F).
- Oil G A lubricating oil with a viscosity of 5.37 08 at 99C (210F) and 33.9 cS at 38C (100F) obtained from a Middle East crude by distillation and extraction of aromatic compounds, followed by solvent dewaxing to a pour point of 9C (16F).
- the alcohols l and II had been obtained by reaction of a mixture of olefins with 8-10 and 11-14 carbon atoms, respectively, with carbon monoxide and hydrogen in the presence of a complex catalyst consisting of cobalt, carbon monoxide and a phosphorus compound.
- composition of alcohols l and II determined with the aid of gas chromatographyand their apparent molecular weight according to their hydroxyl number are given in Tables I and II.
- n-undecyl alcohol 26.0 iso-undecyl alcohol 5.3 alcohols with 11 carbon atoms 0.3 r I I I' l wmge cm a Wash 16 Polymers l and 2 are more actlve than the comparative polymers 3, 4 and 5 in oils which have a viscosity Table II of less than about 10 c5 at 99C (210F) which have been dewaxed to a pour point of about -18C (0F), Composition i.e., oils A-D.
- a lubricating oil composition consisting essentially of a wax-containing hydrocarbon lubricating oil having a viscosity of less than about l0 08 at 210F and dewaxed to a pour point of about 0F or less and from about 0.01 to 2 percent by weight of oil-soluble copoly- Monomer concentration: 42.5%w, leadingto the formation mer of polyalkyl methacrylates having (a) a molar pergs g g z' g z r g f g gi centage of alkyl methacrylates with branched alkyl b jo gmy g chains from 5 to 25 percent, (b) at least eight alkyl Q Y t n hains with a different number of carbon atoms in figlj gfi ggaz Peron e which the number of alkyl chains of 9 carbon atom
- composition of claim 1 in which the percentage of oil-soluble copolymer of polyalkyl methacylates Polymers 1 and 2 come within the scope of the inveni bo t 0,05 to 0.5 percent by weight. tion. Polymer 3 is not according to the invention since 3, Th composition of claim 1 in which the molar the average number of carbon atoms in the side chains is 14, and polymer 4 is not according to the invention percentage of alkyl methacrylates with branched alkyl chains is 5 to 15 percent.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1321171 | 1971-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3869396A true US3869396A (en) | 1975-03-04 |
Family
ID=10018857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US248261A Expired - Lifetime US3869396A (en) | 1971-05-05 | 1972-04-27 | Lubricating oil compositions |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3869396A (cs) |
| JP (1) | JPS5911638B1 (cs) |
| AT (1) | AT323994B (cs) |
| AU (1) | AU464362B2 (cs) |
| BE (1) | BE782598A (cs) |
| CA (1) | CA970100A (cs) |
| DE (1) | DE2221662C2 (cs) |
| FR (1) | FR2135252B1 (cs) |
| GB (1) | GB1347713A (cs) |
| IT (1) | IT955181B (cs) |
| NL (1) | NL169327C (cs) |
| SE (1) | SE383895B (cs) |
| ZA (1) | ZA722994B (cs) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951929A (en) * | 1972-05-08 | 1976-04-20 | Texaco Inc. | Polyacrylates and waxy residual fuel compositions thereof |
| US4045376A (en) * | 1976-04-23 | 1977-08-30 | Texaco Inc. | Synthetic turbine oils |
| US4071678A (en) * | 1976-04-29 | 1978-01-31 | The United States Of America As Represented By The Secretary Of The Army | Random copolymers of methyl methacrylate and N-octadecyl methacrylate |
| US4080304A (en) * | 1975-06-16 | 1978-03-21 | The Dow Chemical Company | Hydrocarbon oil compositions containing polymers to control viscosity temperature relationship |
| US4146492A (en) * | 1976-04-02 | 1979-03-27 | Texaco Inc. | Lubricant compositions which exhibit low degree of haze and methods of preparing same |
| US4776967A (en) * | 1987-02-27 | 1988-10-11 | Idemitsu Kosan Company Limited | Lubricating oil composition |
| US4822508A (en) * | 1985-12-13 | 1989-04-18 | Rohm Gmbh | Shear stable multirange oils having an improved viscosity index |
| US4828731A (en) * | 1987-11-07 | 1989-05-09 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition for working metal |
| US4844829A (en) * | 1987-08-19 | 1989-07-04 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| US4857220A (en) * | 1987-05-14 | 1989-08-15 | Idemitsu Kosan Co., Ltd. | Base oil of lubricating oil for mechanical apparatuses with orifice mechanism |
| US4867894A (en) * | 1986-03-07 | 1989-09-19 | Rohm Gmbh | Pour point improving additives for mineral oils |
| US4956111A (en) * | 1987-08-19 | 1990-09-11 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| EP0329756B1 (en) * | 1987-08-19 | 1994-05-11 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| US5312884A (en) * | 1993-04-30 | 1994-05-17 | Rohm And Haas Company | Copolymer useful as a pour point depressant for a lubricating oil |
| US5726136A (en) * | 1994-10-19 | 1998-03-10 | Agip Petroli S.P.A. | Multifunctional additive for lubricating oils compatible with fluoroelastomers |
| US5955405A (en) * | 1998-08-10 | 1999-09-21 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
| US6114288A (en) * | 1998-05-01 | 2000-09-05 | Shell Research Limited | Lubricating oil composition for internal combustion engines |
| US20060163175A1 (en) * | 2002-06-14 | 2006-07-27 | Oilcare Holding Aps, A Corporation Of Denmark | Process and an apparatus for puritification of waste oil or re-refined oil from mineral or synthetic oil |
| WO2010081634A1 (de) | 2009-01-13 | 2010-07-22 | Evonik Rohmax Additives Gmbh | Kraftstoffzusammensetzungen mit verbessertem trübungspunkt und verbesserten lagerungseigenschaften |
| WO2011035947A1 (en) | 2009-09-25 | 2011-03-31 | Evonik Rohmax Additives Gmbh | A composition to improve cold flow properties of fuel oils |
| WO2011095249A1 (en) | 2010-02-05 | 2011-08-11 | Evonik Rohmax Additives Gmbh | A composition having improved filterability |
| WO2012130535A1 (en) | 2011-03-25 | 2012-10-04 | Evonik Rohmax Additives Gmbh | A composition to improve oxidation stability of fuel oils |
| WO2013062924A3 (en) * | 2011-10-27 | 2013-07-11 | The Lubrizol Corporation | Lubricating composition containing an esterified polymer |
| WO2014118370A1 (en) | 2013-02-04 | 2014-08-07 | Evonik Industries Ag | Cold flow improver with broad applicability in mineral diesel, biodiesel and blends thereof |
| US11028334B2 (en) | 2016-06-28 | 2021-06-08 | China Petroleum & Chemical Corporation | Gradient copolymer, its production and application thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1559952A (en) * | 1977-10-26 | 1980-01-30 | Shell Int Research | Lubricating oil compositions |
| HUT69323A (en) * | 1993-07-23 | 1995-09-28 | Rohm & Haas | Copolymer useful as viskosity index improving additive for hydraulic fluid |
| GB2397611B (en) * | 2003-01-21 | 2007-09-19 | Robert George Glasgow | Adjustable roof ladder workbench |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2628225A (en) * | 1949-12-10 | 1953-02-10 | Standard Oil Dev Co | Polymerization of methacrylate esters with benzoyl peroxide-benzoin-ferric laurate catalyst |
| US3598736A (en) * | 1967-08-30 | 1971-08-10 | Shell Oil Co | Polyalkylmethacrylates as pour point depressants for lubricating oils |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2091627A (en) * | 1934-06-08 | 1937-08-31 | Rohm & Haas | Composition of matter and process |
| US2655479A (en) * | 1949-01-03 | 1953-10-13 | Standard Oil Dev Co | Polyester pour depressants |
| US3252949A (en) * | 1960-12-30 | 1966-05-24 | Monsanto Co | Syndiotactic oil-soluble methacrylate polymers |
-
1971
- 1971-05-05 GB GB1321171*[A patent/GB1347713A/en not_active Expired
-
1972
- 1972-04-25 BE BE782598A patent/BE782598A/xx not_active IP Right Cessation
- 1972-04-27 US US248261A patent/US3869396A/en not_active Expired - Lifetime
- 1972-04-28 IT IT23697/72A patent/IT955181B/it active
- 1972-05-02 JP JP47043399A patent/JPS5911638B1/ja active Granted
- 1972-05-03 AU AU41853/72A patent/AU464362B2/en not_active Expired
- 1972-05-03 NL NLAANVRAGE7205925,A patent/NL169327C/xx not_active IP Right Cessation
- 1972-05-03 DE DE2221662A patent/DE2221662C2/de not_active Expired
- 1972-05-03 CA CA141,226A patent/CA970100A/en not_active Expired
- 1972-05-03 ZA ZA722994A patent/ZA722994B/xx unknown
- 1972-05-03 SE SE7205849A patent/SE383895B/xx unknown
- 1972-05-03 AT AT383372A patent/AT323994B/de not_active IP Right Cessation
- 1972-05-03 FR FR7215689A patent/FR2135252B1/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2628225A (en) * | 1949-12-10 | 1953-02-10 | Standard Oil Dev Co | Polymerization of methacrylate esters with benzoyl peroxide-benzoin-ferric laurate catalyst |
| US3598736A (en) * | 1967-08-30 | 1971-08-10 | Shell Oil Co | Polyalkylmethacrylates as pour point depressants for lubricating oils |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951929A (en) * | 1972-05-08 | 1976-04-20 | Texaco Inc. | Polyacrylates and waxy residual fuel compositions thereof |
| US4080304A (en) * | 1975-06-16 | 1978-03-21 | The Dow Chemical Company | Hydrocarbon oil compositions containing polymers to control viscosity temperature relationship |
| US4146492A (en) * | 1976-04-02 | 1979-03-27 | Texaco Inc. | Lubricant compositions which exhibit low degree of haze and methods of preparing same |
| US4045376A (en) * | 1976-04-23 | 1977-08-30 | Texaco Inc. | Synthetic turbine oils |
| US4071678A (en) * | 1976-04-29 | 1978-01-31 | The United States Of America As Represented By The Secretary Of The Army | Random copolymers of methyl methacrylate and N-octadecyl methacrylate |
| US4822508A (en) * | 1985-12-13 | 1989-04-18 | Rohm Gmbh | Shear stable multirange oils having an improved viscosity index |
| US4867894A (en) * | 1986-03-07 | 1989-09-19 | Rohm Gmbh | Pour point improving additives for mineral oils |
| US4776967A (en) * | 1987-02-27 | 1988-10-11 | Idemitsu Kosan Company Limited | Lubricating oil composition |
| US4857220A (en) * | 1987-05-14 | 1989-08-15 | Idemitsu Kosan Co., Ltd. | Base oil of lubricating oil for mechanical apparatuses with orifice mechanism |
| JPH078990B2 (ja) * | 1987-08-19 | 1995-02-01 | ペンゾイル・プロダクツ・カンパニー | メタクリレート系流動点降下剤類及び組成物 |
| US4844829A (en) * | 1987-08-19 | 1989-07-04 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| US4956111A (en) * | 1987-08-19 | 1990-09-11 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| EP0329756B1 (en) * | 1987-08-19 | 1994-05-11 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| US4828731A (en) * | 1987-11-07 | 1989-05-09 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition for working metal |
| US5312884A (en) * | 1993-04-30 | 1994-05-17 | Rohm And Haas Company | Copolymer useful as a pour point depressant for a lubricating oil |
| US5726136A (en) * | 1994-10-19 | 1998-03-10 | Agip Petroli S.P.A. | Multifunctional additive for lubricating oils compatible with fluoroelastomers |
| US6114288A (en) * | 1998-05-01 | 2000-09-05 | Shell Research Limited | Lubricating oil composition for internal combustion engines |
| US5955405A (en) * | 1998-08-10 | 1999-09-21 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
| US20060163175A1 (en) * | 2002-06-14 | 2006-07-27 | Oilcare Holding Aps, A Corporation Of Denmark | Process and an apparatus for puritification of waste oil or re-refined oil from mineral or synthetic oil |
| WO2010081634A1 (de) | 2009-01-13 | 2010-07-22 | Evonik Rohmax Additives Gmbh | Kraftstoffzusammensetzungen mit verbessertem trübungspunkt und verbesserten lagerungseigenschaften |
| WO2011035947A1 (en) | 2009-09-25 | 2011-03-31 | Evonik Rohmax Additives Gmbh | A composition to improve cold flow properties of fuel oils |
| EP2305753A1 (en) | 2009-09-25 | 2011-04-06 | Evonik RohMax Additives GmbH | A composition to improve cold flow properties of fuel oils |
| US10131776B2 (en) | 2009-09-25 | 2018-11-20 | Evonik Oil Additives Gmbh | Composition to improve cold flow properties of fuel oils |
| WO2011095249A1 (en) | 2010-02-05 | 2011-08-11 | Evonik Rohmax Additives Gmbh | A composition having improved filterability |
| WO2012130535A1 (en) | 2011-03-25 | 2012-10-04 | Evonik Rohmax Additives Gmbh | A composition to improve oxidation stability of fuel oils |
| WO2013062924A3 (en) * | 2011-10-27 | 2013-07-11 | The Lubrizol Corporation | Lubricating composition containing an esterified polymer |
| WO2014118370A1 (en) | 2013-02-04 | 2014-08-07 | Evonik Industries Ag | Cold flow improver with broad applicability in mineral diesel, biodiesel and blends thereof |
| US11028334B2 (en) | 2016-06-28 | 2021-06-08 | China Petroleum & Chemical Corporation | Gradient copolymer, its production and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL169327C (nl) | 1982-07-01 |
| DE2221662A1 (de) | 1973-01-11 |
| JPS5911638B1 (cs) | 1984-03-16 |
| SE383895B (sv) | 1976-04-05 |
| AU4185372A (en) | 1973-11-08 |
| ZA722994B (en) | 1973-02-28 |
| AU464362B2 (en) | 1975-08-21 |
| CA970100A (en) | 1975-06-24 |
| GB1347713A (en) | 1974-02-27 |
| FR2135252B1 (cs) | 1974-09-27 |
| AT323994B (de) | 1975-08-11 |
| NL7205925A (cs) | 1972-11-07 |
| BE782598A (fr) | 1972-10-25 |
| FR2135252A1 (cs) | 1972-12-15 |
| NL169327B (nl) | 1982-02-01 |
| DE2221662C2 (de) | 1987-05-14 |
| IT955181B (it) | 1973-09-29 |
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