US3455896A - Reaction products of sulfurized polybutenes and triglycerides - Google Patents
Reaction products of sulfurized polybutenes and triglycerides Download PDFInfo
- Publication number
- US3455896A US3455896A US577166A US3455896DA US3455896A US 3455896 A US3455896 A US 3455896A US 577166 A US577166 A US 577166A US 3455896D A US3455896D A US 3455896DA US 3455896 A US3455896 A US 3455896A
- Authority
- US
- United States
- Prior art keywords
- sulfur
- sulfurized
- polybutenes
- oil
- oils
- 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
Links
- 229920001083 polybutene Polymers 0.000 title description 12
- 239000007795 chemical reaction product Substances 0.000 title description 5
- 150000003626 triacylglycerols Chemical class 0.000 title description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 30
- 229910052717 sulfur Inorganic materials 0.000 description 29
- 239000011593 sulfur Substances 0.000 description 29
- 239000003921 oil Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000005555 metalworking Methods 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 239000000470 constituent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 239000010685 fatty oil Substances 0.000 description 5
- 239000010699 lard oil Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005987 sulfurization reaction Methods 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000010730 cutting oil Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/36—Sulfonation; Sulfation
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
-
- 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
- C10N2040/20—Metal working
-
- 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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
Definitions
- This invention relates to an improved sulfur-containing lubricant additives suitable for use in preparing lubricating oil compositions having improved extreme pressure properties for metalworking purposes.
- Mineral lubricating oils containing sulfurized addition agents have been extensively used as metalworking lubricants and especially as cutting oils.
- the mineral oil component of such lubricants contain constituents that may be toxic or carcinogenic in nature and therefore undesriable due to the potential harm that might occur when brought in contact with the human body.
- the polycyclic aromatic constituents naturally present in most mineral lubricating oils are the undesirable constituents. Accordingly, it is necessary to remove these constituents from the oil in order to have a mineral lubricating oil suitable for the preparation of metalworking oils that are not harmful to the human bdoy.
- the polycyclic aromatics are highly polar and can be removed by suitable solvent extraction methods well known to the art.
- Naturally occurring parafiinic or naphthenic petroleum oils or solvent extracted oils contain less than about percent carbon in aromatic bonding, as determined by the n-d-M Method used for determining the hydrocarbon type analysis of lubricating oils, have been found to be relatively free of toxicity and carcinogenicity characteristics.
- a description of the n-d-M Method may be found on p. 226 of Physical Chemistry of Lubricating Oils by A. Bondi, Reinhold Publishing Corp., New York, 1951.
- Such oils containing minor amounts of the polar aromatic constituents are relatively poor solvents for organic sulfur compounds.
- Such oils are now used as the principal component of commercial metalworking lubricants.
- Conventional sulfurized liquid triglycerides such as the naturally occurring fatty oils of animal, vegetable, or mineral origin, are well-known additives for use in the preparation of mineral oil-based metalworking lubricants. Due to the change of the mineral oil used as the base for making compounded metalworking lubricants and the lack of solvency characteristics thereof, it is not possible to form satisfactory oil blends of the mineral oil and the sulfurized fatty oils so as to incorporate sulfur in amounts greater than about one weight percent of sulfur. In other words, the prior art sulfurized fatty oils are substantially insoluble in the aforesaid mineral oils containing minor amounts of polar aromatic constituents. The use of the sulfurized fatty oils are desirable for imparting additional lubricity to the mineral oil metalworking fluids.
- the desirable properties of the liquid triglycerides can be obtained by reacting the liquid triglyceride in volume proportions of about 0.5-1.5 parts by volume "ice per volume of sulfurized low molecular weight polybutenes having a viscosity of about 60-150 SSU at F., a sulfur content of about 12-20 weight percent, a minimum flash point, COC, of about 220 F., a maximum ASTM D-lSOO color of about 8, and a gravity of about 1828 API at temperatures in the range of about 250- 400" F. for a period of at least 5 minutes to form a sulfurcontaining reaction product that is soluble in mineral oils having poor solvency characteristics. While any liquid triglyceride susceptable to sulfurization can be used to form the desirable oil-soluble sulfur addition agent, lard oil is preferred.
- the aforesaid reaction product provides sulfur that may be very active or relatively inactive so as to provide the desired sulfur activity in the blended oil for light or heavy duty applications.
- sulfur When sulfur is present in a form that readily stains copper, it is called active sulfur.
- the sulfur activity in the additive of this invention can be varied by the temperature and time of reaction. At lower temperatures and times the sulfur is in an extremely active form; and when the reaction is carried out at the higher temperatures and longer periods of time, the activity of the sulfur is reduced. Sulfur activity is determined by heating the blended oil in the presence of copper turnings at 350 F. for 20 hours. The residual sulfur in the oil after the heating period is inactive sulfur, and the difference between the residual sulfur and the initial sulfur content represents active sulfur.
- Preparation of the sulfurized polybutene reactant is effected in accordance with conventional sulfurizing techniques with elemental sulfur. Inasmuch as light color in the sulfurized product is desired so as to minimize darkening of the base oil to which it is added, it has been found that polybutenes having average molecular Weight of 300 or less be used.
- the polybutenes are prepared by known polymerization techniques for polymerizing butene or isobutene feedstocks.
- the preferred polybutenes used in the present invention are a mixture of butene dimers, trimers, tetramers, or pentamers, i.e.
- the effectiveness of the additive concentrate of this invention in blended metalworking oils, and to obtain the requisite load-bearing or extreme pressure properties of such blended oils, is determined by the active sulfur content of the additive. -It has been found that at least one weight percent of the total sulfur in the additive should be in the active form.
- a series of cutting oil blends containing solvent extracted SAE 10 grade mineral oil and various levels of the aforesaid sulfurized polymer-lard oil reaction product were prepared to provide sulfur contents ranging from one to three percent in the blends. These blends were subjected to temperature cycles between 0 and 40 F.
- this invention provides a satisfactory sulfurized additive containing fatty oils that are completely soluble in solvent extracted mineral oils that can be used to form satisfactory metalworking lubricants.
- the oil-soluble sulfur-containing reaction product produced by the process of reacting (A) sulfurized low molecular weight polybutenes having a viscosity of about 60-150 SSU at 100 F., a sulfur content of about 1220 weight percent, a minimum flash point, COC, of about 220 F., a maximum ASTM D-1500 color of about 8, and a gravity of about 1828 API; and (B) from about 0.5 to about 1.5 parts by volume per part by volume of reactant A of liquid triglyceride susceptible to sulfurization at a temperature in the range of about 250400 F. for a period of at least five minutes.
- reactant B is lard oil
- polybutenes are mixtures of butene polymers containing 8 to 20 carbon atoms in the polymer chain.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
United States Patent US. Cl. 260-125 4 Claims ABSTRACT OF THE DISCLOSURE Sulfur-containing oil-soluble extreme pressure additives for lubricants are produced by reacting one part by volume of sulfurized low molecular weight polybutenes and 0.5 to 1.5 parts by volume of liquid triglycerides susceptable to sulfurization at a temperature of about 250-400 F. for a period of at least 5 minutes.
This invention relates to an improved sulfur-containing lubricant additives suitable for use in preparing lubricating oil compositions having improved extreme pressure properties for metalworking purposes.
Mineral lubricating oils containing sulfurized addition agents have been extensively used as metalworking lubricants and especially as cutting oils. In recent years, it has been found that the mineral oil component of such lubricants contain constituents that may be toxic or carcinogenic in nature and therefore undesriable due to the potential harm that might occur when brought in contact with the human body. It has been found that the polycyclic aromatic constituents naturally present in most mineral lubricating oils are the undesirable constituents. Accordingly, it is necessary to remove these constituents from the oil in order to have a mineral lubricating oil suitable for the preparation of metalworking oils that are not harmful to the human bdoy. The polycyclic aromatics are highly polar and can be removed by suitable solvent extraction methods well known to the art. Naturally occurring parafiinic or naphthenic petroleum oils or solvent extracted oils contain less than about percent carbon in aromatic bonding, as determined by the n-d-M Method used for determining the hydrocarbon type analysis of lubricating oils, have been found to be relatively free of toxicity and carcinogenicity characteristics. A description of the n-d-M Method may be found on p. 226 of Physical Chemistry of Lubricating Oils by A. Bondi, Reinhold Publishing Corp., New York, 1951. Such oils containing minor amounts of the polar aromatic constituents are relatively poor solvents for organic sulfur compounds. Such oils are now used as the principal component of commercial metalworking lubricants.
Conventional sulfurized liquid triglycerides, such as the naturally occurring fatty oils of animal, vegetable, or mineral origin, are well-known additives for use in the preparation of mineral oil-based metalworking lubricants. Due to the change of the mineral oil used as the base for making compounded metalworking lubricants and the lack of solvency characteristics thereof, it is not possible to form satisfactory oil blends of the mineral oil and the sulfurized fatty oils so as to incorporate sulfur in amounts greater than about one weight percent of sulfur. In other words, the prior art sulfurized fatty oils are substantially insoluble in the aforesaid mineral oils containing minor amounts of polar aromatic constituents. The use of the sulfurized fatty oils are desirable for imparting additional lubricity to the mineral oil metalworking fluids.
It has been found, in accordance with the present invention, that the desirable properties of the liquid triglycerides can be obtained by reacting the liquid triglyceride in volume proportions of about 0.5-1.5 parts by volume "ice per volume of sulfurized low molecular weight polybutenes having a viscosity of about 60-150 SSU at F., a sulfur content of about 12-20 weight percent, a minimum flash point, COC, of about 220 F., a maximum ASTM D-lSOO color of about 8, and a gravity of about 1828 API at temperatures in the range of about 250- 400" F. for a period of at least 5 minutes to form a sulfurcontaining reaction product that is soluble in mineral oils having poor solvency characteristics. While any liquid triglyceride susceptable to sulfurization can be used to form the desirable oil-soluble sulfur addition agent, lard oil is preferred.
The aforesaid reaction product provides sulfur that may be very active or relatively inactive so as to provide the desired sulfur activity in the blended oil for light or heavy duty applications. When sulfur is present in a form that readily stains copper, it is called active sulfur. The sulfur activity in the additive of this invention can be varied by the temperature and time of reaction. At lower temperatures and times the sulfur is in an extremely active form; and when the reaction is carried out at the higher temperatures and longer periods of time, the activity of the sulfur is reduced. Sulfur activity is determined by heating the blended oil in the presence of copper turnings at 350 F. for 20 hours. The residual sulfur in the oil after the heating period is inactive sulfur, and the difference between the residual sulfur and the initial sulfur content represents active sulfur.
Preparation of the sulfurized polybutene reactant is effected in accordance with conventional sulfurizing techniques with elemental sulfur. Inasmuch as light color in the sulfurized product is desired so as to minimize darkening of the base oil to which it is added, it has been found that polybutenes having average molecular Weight of 300 or less be used. The polybutenes are prepared by known polymerization techniques for polymerizing butene or isobutene feedstocks. The preferred polybutenes used in the present invention are a mixture of butene dimers, trimers, tetramers, or pentamers, i.e. mixture of butene polymers containing 8 to 20 carbon atoms in the polymer chain, obtained as by-product from the polylmerization of butene for the preparation of higher molecular weight commercial polybutenes. After sulfurization reaction is completed, the reaction mixture is stripped to remove unreacted polybutenes and then filtered to remove unreacted sulfur.
It has been found that steam stripping of the reaction mixture of the polymer and liquid triglyceride substantially improves the color and odor properties of the sulfurized additive of this invention.
The reaction of a mixture containing seven percent sulfur formed by admixing 45 parts of the sulfurized polybutene and 55 parts (by volume) of lard oil at 325 F. for one hour, followed by stripping to remove volatile by-products formed a sulfurized additive containing about 50 percent active sulfur.
The effectiveness of the additive concentrate of this invention in blended metalworking oils, and to obtain the requisite load-bearing or extreme pressure properties of such blended oils, is determined by the active sulfur content of the additive. -It has been found that at least one weight percent of the total sulfur in the additive should be in the active form.
A series of cutting oil blends containing solvent extracted SAE 10 grade mineral oil and various levels of the aforesaid sulfurized polymer-lard oil reaction product were prepared to provide sulfur contents ranging from one to three percent in the blends. These blends were subjected to temperature cycles between 0 and 40 F.
to determine whether separation of the sulfurized material would occur. No separation was found in contrast to similar blends containing conventional sulfurized lard oil having equivalent sulfur content, which blends immediately separated. Accordingly, this invention provides a satisfactory sulfurized additive containing fatty oils that are completely soluble in solvent extracted mineral oils that can be used to form satisfactory metalworking lubricants.
We claim:
1. The oil-soluble sulfur-containing reaction product produced by the process of reacting (A) sulfurized low molecular weight polybutenes having a viscosity of about 60-150 SSU at 100 F., a sulfur content of about 1220 weight percent, a minimum flash point, COC, of about 220 F., a maximum ASTM D-1500 color of about 8, and a gravity of about 1828 API; and (B) from about 0.5 to about 1.5 parts by volume per part by volume of reactant A of liquid triglyceride susceptible to sulfurization at a temperature in the range of about 250400 F. for a period of at least five minutes.
2. The product of claim 1 wherein reactant B is lard oil.
3. The product of claim 1 containing at least 1.0 weight percent active sulfur.
4. The product of claim 2 wherein said polybutenes are mixtures of butene polymers containing 8 to 20 carbon atoms in the polymer chain.
References Cited UNITED STATES PATENTS 3,133,022 5/1964 Sabol et al. 260139 CHARLES B. PARKER, Primary Examiner D. R. PHILLIPS, Assistant Examiner US. Cl X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57716666A | 1966-09-06 | 1966-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3455896A true US3455896A (en) | 1969-07-15 |
Family
ID=24307535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US577166A Expired - Lifetime US3455896A (en) | 1966-09-06 | 1966-09-06 | Reaction products of sulfurized polybutenes and triglycerides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3455896A (en) |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7202158A (en) * | 1971-02-19 | 1972-08-22 | ||
| DE2207747A1 (en) * | 1971-02-19 | 1972-10-19 | Sun Research And Development Co., Philadelphia, Pa. (V.St.A.) | Sulphurised triglyceride - olefin mixt - as substitute for sulphurised sperm oil |
| DE2235608A1 (en) * | 1971-07-26 | 1973-02-08 | Chevron Res | LUBRICANT |
| DE2307600A1 (en) * | 1972-03-20 | 1973-10-04 | Elco Corp | HIGH PRESSURE LUBRICANT ADDITIVE |
| US3926822A (en) * | 1971-09-08 | 1975-12-16 | Lubrizol Corp | Novel sulfur-containing compositions |
| US3963692A (en) * | 1974-06-27 | 1976-06-15 | Lubricaton Company Of America | Sulfur-chlorinated polynuclear aromatic and fat mixture |
| US4166796A (en) * | 1971-04-19 | 1979-09-04 | Suntech, Inc. | Composition comprising a cosulfurized blend of lard oil and an olefin |
| US4166795A (en) * | 1971-04-26 | 1979-09-04 | Suntech, Inc. | Chemical reaction product of sulfur, lard oil and polyisobutylene |
| US4166797A (en) * | 1971-04-19 | 1979-09-04 | Suntech, Inc. | Oil containing a consulfurized olefin-triglyceride blend |
| US4188300A (en) * | 1973-04-05 | 1980-02-12 | Mayco Oil And Chemical Company, Inc. | Cosulfurized olefin and lard oil |
| US4321153A (en) * | 1971-04-19 | 1982-03-23 | Suntech, Inc. | Process of sulfurizing triglyceride and an olefin |
| US4380499A (en) * | 1981-08-10 | 1983-04-19 | Ferro Corporation | Sulfurized fatty oil additives and their use in a lubricating oil and a fuel |
| US4380498A (en) * | 1981-08-10 | 1983-04-19 | Ferro Corporation | Sulfurized, transesterified oil additives and their use in a lubricating oil and a fuel |
| US4456540A (en) * | 1979-06-18 | 1984-06-26 | Sun Tech, Inc. | Process of sulfurizing triglyceride and an olefin |
| US4481140A (en) * | 1971-02-19 | 1984-11-06 | Sun Research And Development Co. | Process of sulfurizing lard oil and an olefin and resultant product |
| US4487705A (en) * | 1971-02-19 | 1984-12-11 | Sun Ventures, Inc. | Oil containing a cosulfurized olefin-triglyceride blend |
| EP0208513A3 (en) * | 1985-07-08 | 1987-09-16 | Ethyl Petroleum Additives, Inc. | Lubricating compositions |
| US4921624A (en) * | 1988-06-03 | 1990-05-01 | Ferro Corporation | Modified fatty amides and sulfurized fatty oils as lubricant additives |
| US4959168A (en) * | 1988-01-15 | 1990-09-25 | The Lubrizol Corporation | Sulfurized compositions, and additive concentrates and lubricating oils containing same |
| US4970010A (en) * | 1988-07-19 | 1990-11-13 | International Lubricants, Inc. | Vegetable oil derivatives as lubricant additives |
| US5124055A (en) * | 1988-03-31 | 1992-06-23 | Ethyl Petroleum Additives, Inc. | Lubricating oil composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133022A (en) * | 1958-09-04 | 1964-05-12 | Standard Oil Co | Lubricant additive and composition containing same |
-
1966
- 1966-09-06 US US577166A patent/US3455896A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133022A (en) * | 1958-09-04 | 1964-05-12 | Standard Oil Co | Lubricant additive and composition containing same |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2207747A1 (en) * | 1971-02-19 | 1972-10-19 | Sun Research And Development Co., Philadelphia, Pa. (V.St.A.) | Sulphurised triglyceride - olefin mixt - as substitute for sulphurised sperm oil |
| US4487705A (en) * | 1971-02-19 | 1984-12-11 | Sun Ventures, Inc. | Oil containing a cosulfurized olefin-triglyceride blend |
| US4481140A (en) * | 1971-02-19 | 1984-11-06 | Sun Research And Development Co. | Process of sulfurizing lard oil and an olefin and resultant product |
| NL7202158A (en) * | 1971-02-19 | 1972-08-22 | ||
| US4321153A (en) * | 1971-04-19 | 1982-03-23 | Suntech, Inc. | Process of sulfurizing triglyceride and an olefin |
| US4166797A (en) * | 1971-04-19 | 1979-09-04 | Suntech, Inc. | Oil containing a consulfurized olefin-triglyceride blend |
| US4166796A (en) * | 1971-04-19 | 1979-09-04 | Suntech, Inc. | Composition comprising a cosulfurized blend of lard oil and an olefin |
| US4166795A (en) * | 1971-04-26 | 1979-09-04 | Suntech, Inc. | Chemical reaction product of sulfur, lard oil and polyisobutylene |
| DE2235608A1 (en) * | 1971-07-26 | 1973-02-08 | Chevron Res | LUBRICANT |
| US3953347A (en) * | 1971-09-08 | 1976-04-27 | The Lubrizol Corporation | Novel sulfur-containing compositions |
| US3926822A (en) * | 1971-09-08 | 1975-12-16 | Lubrizol Corp | Novel sulfur-containing compositions |
| US4149982A (en) * | 1972-03-20 | 1979-04-17 | The Elco Corporation | Extreme pressure additives for lubricants |
| DE2307600A1 (en) * | 1972-03-20 | 1973-10-04 | Elco Corp | HIGH PRESSURE LUBRICANT ADDITIVE |
| US4188300A (en) * | 1973-04-05 | 1980-02-12 | Mayco Oil And Chemical Company, Inc. | Cosulfurized olefin and lard oil |
| US3963692A (en) * | 1974-06-27 | 1976-06-15 | Lubricaton Company Of America | Sulfur-chlorinated polynuclear aromatic and fat mixture |
| US4456540A (en) * | 1979-06-18 | 1984-06-26 | Sun Tech, Inc. | Process of sulfurizing triglyceride and an olefin |
| US4380499A (en) * | 1981-08-10 | 1983-04-19 | Ferro Corporation | Sulfurized fatty oil additives and their use in a lubricating oil and a fuel |
| US4380498A (en) * | 1981-08-10 | 1983-04-19 | Ferro Corporation | Sulfurized, transesterified oil additives and their use in a lubricating oil and a fuel |
| EP0208513A3 (en) * | 1985-07-08 | 1987-09-16 | Ethyl Petroleum Additives, Inc. | Lubricating compositions |
| US4959168A (en) * | 1988-01-15 | 1990-09-25 | The Lubrizol Corporation | Sulfurized compositions, and additive concentrates and lubricating oils containing same |
| US5124055A (en) * | 1988-03-31 | 1992-06-23 | Ethyl Petroleum Additives, Inc. | Lubricating oil composition |
| US4921624A (en) * | 1988-06-03 | 1990-05-01 | Ferro Corporation | Modified fatty amides and sulfurized fatty oils as lubricant additives |
| US4970010A (en) * | 1988-07-19 | 1990-11-13 | International Lubricants, Inc. | Vegetable oil derivatives as lubricant additives |
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