US3458444A - Rust inhibiting composition - Google Patents
Rust inhibiting composition Download PDFInfo
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- US3458444A US3458444A US683774A US3458444DA US3458444A US 3458444 A US3458444 A US 3458444A US 683774 A US683774 A US 683774A US 3458444D A US3458444D A US 3458444DA US 3458444 A US3458444 A US 3458444A
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- Prior art keywords
- rust
- reaction product
- lubricating oil
- anhydride
- sludge
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- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
- C10N2040/135—Steam engines or turbines
Definitions
- This invention relates to a novel rust inhibiting composition formed by the reaction of an alkenyl succinic acid and/or anhydride with an alkanolamine and to a turbine lubricating oil composition containing the rust inhibitor.
- Alkenyl succinic acids and anhydrides have heretofore been reacted with aliphatic amines and with certain alkanolamines in conjunction with aliphatic acids to produce reaction products exhibiting rust inhibiting properties, see US. 2,540,800 and U.S. 2,638,449.
- the level of rust inhibition imparted by these materials has not been entirely satisfactory.
- some of the known reaction products have been ineffective for preventing the formation of sludge when employed in a turbine lubricating oil composition.
- the reaction product of the present invention is highly elfective as a rust inhibitor in the ASTM Turbine Oil Oxidation Test (D-943) and, surprisingly, also for reducing or substantially preventing the formation of sludge in a turbine lubricating oil composition.
- a rust inhibitor comprising the reaction product of a reactant, selected from the group consisting of an alkenyl succinic acid and an alkenyl succinic anhydride in which the alkenyl radical has from 8 to 18 carbon atoms, and a tertiary amine compound, represented by the formula:
- R is an aryl or alkaryl radical having from 6 to carbon atoms and R represents a divalent alkylene radical having from 2 to 4 carbon atoms, in a mole ratio ranging from about 1:1 to 2:1 respectively, and at a temperature from about 80 to about 125 C.
- a rust and sludge inhibited turbine lubricating oil composition comprising a major proportion of mineral lubricating oil with conventional additives and a minor amount of the reaction product defined above.
- alkenyl succinic acid and anhydride components employed in making the additive of the invention are represented by the following formulas:
- R represents an alkenyl radical having from 8 to 18 carbon atoms.
- Typical alkenyl succinic acids or "ice anhydrides which can be employed are dodecenyl succinic acid and anhydride decenyl succinic acid and anhydride, tetradecenyl succinic acid and anhydride and the like.
- the tertiary amine component of the reaction product is represented by the formula:
- R is an aryl or alkaryl radical having from 6 to 10 carbon atoms and R represents a divalent alkylene radical having from 2 to 4 carbon atoms.
- R represents an aryl or alkaryl radical having from 6 to 10 carbon atoms and R represents a divalent alkylene radical having from 2 to 4 carbon atoms.
- the presence of an aryl -or alkaryl radical on the nitrogen atom in the alkanolamine component of the reaction product appears to be essential to the preparation of an effective rustinhibiting and sludge-inhibiting reaction product which does not degrade other desired properties possessed by a turbine lubricating oil.
- reaction products in which R is an alkyl radical on the nitrogen atom have the undesirable property of degrading water separating characteristics of the turbine oil composition.
- Tertiary amine compounds which will form effective rust and sludge inhibiting reaction products include: phenyldiethanolamine, tolyldiethanolamine, isopropylphenyl diethanolamine, ethylphenyl diethanolamine, phenyl dipropanolamine and the like.
- the rust inhibiting reaction product of the invention is prepared by reacting the alkenyl succinic acid or anhydride and the above-defined tertiary amine in approximately 1:1 to 2:1 mole ratios respectively.
- the components of the reaction product are admixed either With or without the aid of a mutual solvent and reacted at a temperature from about to about C.
- a catalyst such as p-toluene sulfonic acid can be used to promote reaction.
- EXAMPLE I 830 grams (4.58 moles) of N-phenyl diethanolamine were dissolved in 2200 ml. of benzene and heated at reflux temperature for about 2 hrs. to remove the water present in the ethanolamine. 1220 grams (4.58 moles) of dodecenyl succinic anhydride were added to the ben zene solution over 80 minutes while the solution was maintained at a temperature from 188204 F. After all ofthe anhydride had been added, the reaction was continued for about 4 hours at about ZOO-201 F. The benzene was then removed by distillation and by blowing nitrogen through the reaction product. 2063 grams of the reaction product (Additive A) was recovered having a Neutralization No. of 121 as compared to a calculated Neut. No. of 126.
- the lubricating oil composition of the invention comprises a refined mineral lubricating oil containing conventional turbine oil additives and from about 0.01 to 5 weight percent of the reaction product of the invention.
- the preferred concentration of the reaction product in the lubricating oil is from about 0.025 to 0.5 weight percent.
- the reaction product is readily soluble in mineral lubricating oils and can be readily blended therein to prepare the lubricating composition.
- a turbine lubricating oil composition comprising a acteristics of steam-turbine oils.
- the base blends emmapor proportion of a mineral lubricating oil and a minor ploye in h e tests, Bl n A r gh D, Wer refi rust inhibiting amount of the reaction product of a reactparaffin base mineral oils containing 0.30 weight percent ant selected from the group consisting of an alkenyl sucditertiary butyl cresol, 0.033 weight percent tetrapropenyl cinic acid and an alkenyl succinic anhydride in which the succinic acid, and 6 ppm.
- silicone polymer which are alkenyl radical has from 8 to 18 carbon atoms, and a terwidely used in inhibit oxidation, rusting, and foaming, tiary amine reactant represented by the formula: respetively in steam turbine oils.
- Base Blend E was the same as Base Blend C plus 0.1 weight percent of an 2 alkylated aromatic aimine added as supplemental oxidation in which R 1s an aryl or alkaryl radical having from 6 to inhibitor.
- These base blends had the following charac- 10 carbon atoms and R is a divalent alkylene radical havteristics. ing from 2 to 4 carbon atoms in a mole ratio ranging from Base Blend A B O D E Gravity, API 30.
- the Oxidation Test was run until the acidity of the about 1:1 to 2:1 respectively and at a temperature rangoil sample reached a Neutralization No. of 2.0. The ing from about 80 to about 125 C. length of time it took to reach this end point is given in 2.
- a lubricating oil composition according to claim 1 in which said alkenyl succinic anhydride is dodecenyl ASTM OXIDATION TEST succinic anhydride and said reaction is conducted using Hours a mole ratio of about 1:1.
- a lubricating oil composition according to claim 1 Base blend Additivewh percent i ⁇ ? Rust Sludge 40 in 1which said tertiary amine reactant is N-phenyl diethano amine. f: 'gfifgag figg'gj 31$ 532 32 5.
- a lubricating oil composition according to claim 1 (125 AdtliiiveB 31092 None None containing from about 0.05 to 1 weight percent of diter- 3 3,: I "gififiiffffff i: 3 3; 2 3; tiary butyl cresol and from about 0.01 to 0.15 weight per- D 0.05 Add't' A 2,602 None No e 3 iff 1,720 664 6 cent of tetrapropenyl SUCClIllC acid.
Description
United States Patent 3,458,444 RUST INHIBITING COMPOSITION William T. Shepherd, Port Arthur, Howard J. Platte, Groves, and Federico P. Gonzalez, Nederland, Tex., assignors to Texaco Inc., New York, N.Y., a corporation of Delaware No Drawing. Filed Nov. 17, 1967, Ser. No. 683,774 Int. Cl. Clllm 1/32; C23f 11/14 U.S. Cl. 252-51.5 Claims ABSTRACT OF THE DISCLOSURE Rust and sludge inhibiting additive for mineral lubricating oils comprising the reaction product of an alkenyl succinic acid or anhydride and a tertiary amine represented by the formula RN(R'OH) in which R is an aryl or alkaryl radical and R is a divalent alkylene radical having from 2 to 4 carbon atoms and mineral lubricating oil composition containing said rust and sludge inhibitor.
This invention relates to a novel rust inhibiting composition formed by the reaction of an alkenyl succinic acid and/or anhydride with an alkanolamine and to a turbine lubricating oil composition containing the rust inhibitor.
Alkenyl succinic acids and anhydrides have heretofore been reacted with aliphatic amines and with certain alkanolamines in conjunction with aliphatic acids to produce reaction products exhibiting rust inhibiting properties, see US. 2,540,800 and U.S. 2,638,449. The level of rust inhibition imparted by these materials, however, has not been entirely satisfactory. In addition, some of the known reaction products have been ineffective for preventing the formation of sludge when employed in a turbine lubricating oil composition. In contrast to the known rust inhibitors, the reaction product of the present invention is highly elfective as a rust inhibitor in the ASTM Turbine Oil Oxidation Test (D-943) and, surprisingly, also for reducing or substantially preventing the formation of sludge in a turbine lubricating oil composition.
In accordance with this invention, there is provided a rust inhibitor comprising the reaction product of a reactant, selected from the group consisting of an alkenyl succinic acid and an alkenyl succinic anhydride in which the alkenyl radical has from 8 to 18 carbon atoms, and a tertiary amine compound, represented by the formula:
in which R is an aryl or alkaryl radical having from 6 to carbon atoms and R represents a divalent alkylene radical having from 2 to 4 carbon atoms, in a mole ratio ranging from about 1:1 to 2:1 respectively, and at a temperature from about 80 to about 125 C. There is also provided a rust and sludge inhibited turbine lubricating oil composition comprising a major proportion of mineral lubricating oil with conventional additives and a minor amount of the reaction product defined above.
The alkenyl succinic acid and anhydride components employed in making the additive of the invention are represented by the following formulas:
in which R represents an alkenyl radical having from 8 to 18 carbon atoms. Typical alkenyl succinic acids or "ice anhydrides which can be employed are dodecenyl succinic acid and anhydride decenyl succinic acid and anhydride, tetradecenyl succinic acid and anhydride and the like.
The tertiary amine component of the reaction product is represented by the formula:
in which R is an aryl or alkaryl radical having from 6 to 10 carbon atoms and R represents a divalent alkylene radical having from 2 to 4 carbon atoms. The presence of an aryl -or alkaryl radical on the nitrogen atom in the alkanolamine component of the reaction product appears to be essential to the preparation of an effective rustinhibiting and sludge-inhibiting reaction product which does not degrade other desired properties possessed by a turbine lubricating oil. For example, reaction products in which R is an alkyl radical on the nitrogen atom have the undesirable property of degrading water separating characteristics of the turbine oil composition.
Tertiary amine compounds which will form effective rust and sludge inhibiting reaction products include: phenyldiethanolamine, tolyldiethanolamine, isopropylphenyl diethanolamine, ethylphenyl diethanolamine, phenyl dipropanolamine and the like.
The rust inhibiting reaction product of the invention is prepared by reacting the alkenyl succinic acid or anhydride and the above-defined tertiary amine in approximately 1:1 to 2:1 mole ratios respectively. The components of the reaction product are admixed either With or without the aid of a mutual solvent and reacted at a temperature from about to about C. A catalyst, such as p-toluene sulfonic acid can be used to promote reaction.
The following examples illustrate the preparation of the reaction product of the invention.
EXAMPLE I 830 grams (4.58 moles) of N-phenyl diethanolamine were dissolved in 2200 ml. of benzene and heated at reflux temperature for about 2 hrs. to remove the water present in the ethanolamine. 1220 grams (4.58 moles) of dodecenyl succinic anhydride were added to the ben zene solution over 80 minutes while the solution was maintained at a temperature from 188204 F. After all ofthe anhydride had been added, the reaction was continued for about 4 hours at about ZOO-201 F. The benzene was then removed by distillation and by blowing nitrogen through the reaction product. 2063 grams of the reaction product (Additive A) was recovered having a Neutralization No. of 121 as compared to a calculated Neut. No. of 126.
EXAMPLE II 27.4 grams (0.20 mole) of N-phenyl diethanolamine were dissolved in 300 m1. of benzene and heated at reflux temperature to remove water. 106.4 grams (0.40 mole) of dodecenyl succinic anhydride were added to the benzene solution and the mixture reacted at a temperature from 180 to 184 F. for 2 hours. The benzene was removed by distillation and grams of product recovered (Additive B) having a Neutralization No. of as compared to a calculated Neut. No. of 168.
The lubricating oil composition of the invention comprises a refined mineral lubricating oil containing conventional turbine oil additives and from about 0.01 to 5 weight percent of the reaction product of the invention. The preferred concentration of the reaction product in the lubricating oil is from about 0.025 to 0.5 weight percent. The reaction product is readily soluble in mineral lubricating oils and can be readily blended therein to prepare the lubricating composition.
The rust-inhibiting and sludge-inhibiting properties of the reaction product of the invention were determined in the ASTM Oxidation Test (D-943) wherein the oil sample is subject to a temperature of 95 C. in the presence of water, oxygen and an iron-copper catalyst. This test Obviously numerous modifications and variations of the invention may be made without departing from the spirit and scope thereof, and therefore, only such limitations should be made as are indicated in the appended claims.
We claim:
is particularly designed to determine the oxidation char- 5 1. A turbine lubricating oil composition comprising a acteristics of steam-turbine oils. The base blends emmapor proportion of a mineral lubricating oil and a minor ploye in h e tests, Bl n A r gh D, Wer refi rust inhibiting amount of the reaction product of a reactparaffin base mineral oils containing 0.30 weight percent ant selected from the group consisting of an alkenyl sucditertiary butyl cresol, 0.033 weight percent tetrapropenyl cinic acid and an alkenyl succinic anhydride in which the succinic acid, and 6 ppm. silicone polymer, which are alkenyl radical has from 8 to 18 carbon atoms, and a terwidely used in inhibit oxidation, rusting, and foaming, tiary amine reactant represented by the formula: respetively in steam turbine oils. Base Blend E was the same as Base Blend C plus 0.1 weight percent of an 2 alkylated aromatic aimine added as supplemental oxidation in which R 1s an aryl or alkaryl radical having from 6 to inhibitor. These base blends had the following charac- 10 carbon atoms and R is a divalent alkylene radical havteristics. ing from 2 to 4 carbon atoms in a mole ratio ranging from Base Blend A B O D E Gravity, API 30. 0-33.0 20.0-32.0 28.5-31.5 27.0-30.0 23.5-31.5 Flash GOO, F. (min). 300 400 410 60 410 Vis.SUS at 100 F 140-15 200-225 300-315 650-700 300-315 Color ASTM (max.) 1. 0 1.0 1.0 2. 0 1. 0 Pour, F. (max.) 0 5 5 5 5 Neut. No. (man) 0. 10 0. 1o 0. 10 0. 10 0. 10
The Oxidation Test was run until the acidity of the about 1:1 to 2:1 respectively and at a temperature rangoil sample reached a Neutralization No. of 2.0. The ing from about 80 to about 125 C. length of time it took to reach this end point is given in 2. A lubricating oil composition according to claim 1 hours. Likewise, the time to formation of rust on the steel containing from about 0.01 to 5 weight percent of said coils and sludge in the oil is shown in hours. The results reaction product. are the average for two or more test samples. 3. A lubricating oil composition according to claim 1 in which said alkenyl succinic anhydride is dodecenyl ASTM OXIDATION TEST succinic anhydride and said reaction is conducted using Hours a mole ratio of about 1:1.
4. A lubricating oil composition according to claim 1 Base blend Additivewh percent i}? Rust Sludge 40 in 1which said tertiary amine reactant is N-phenyl diethano amine. f: 'gfifgag figg'gj 31$ 532 32 5. A lubricating oil composition according to claim 1 (125 AdtliiiveB 31092 None None containing from about 0.05 to 1 weight percent of diter- 3 3,: I "gififiiffffff i: 3 3; 2 3; tiary butyl cresol and from about 0.01 to 0.15 weight per- D 0.05 Add't' A 2,602 None No e 3 iff 1,720 664 6 cent of tetrapropenyl SUCClIllC acid.
on 0113i 1, E 8 32; 95: References Cited 1, 0 B 2 gig g g UNITED STATES PATENTS n o e oilfg None 27800 3 8 3 2,588,412 3/1952 Rocch n Do 0.03 AdditiveA 3,222 None None 2,604,451 7/1952 Rocchim. Do 0.025 Additive B 2, 940 None None 3 183 070 5/1965 Udelhofem 3,368,971 2/1968 Retzlotf et al. The foregoing test results show that the reaction prodnets of the invention very substantially improved the oxi- DANIEL WYMAN Pnmary Exammer dation resistance of the lubricating oil composition. More surprisingly these anti-rust agents completely arrested the formation of rust and the deposition of sludge in the improved lubricating oils.
W. J. SHINE, Assistant Examiner U.S. Cl. X.R. 252-392, 403
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US68377467A | 1967-11-17 | 1967-11-17 |
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US3458444A true US3458444A (en) | 1969-07-29 |
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US683774A Expired - Lifetime US3458444A (en) | 1967-11-17 | 1967-11-17 | Rust inhibiting composition |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081388A (en) * | 1975-04-18 | 1978-03-28 | Orogil | Compositions based on alkenylsuccinimides as additives for lubricating oils |
US4208293A (en) * | 1978-11-13 | 1980-06-17 | Ethyl Corporation | Improved crankcase lubricant composition |
US4325827A (en) * | 1981-01-26 | 1982-04-20 | Edwin Cooper, Inc. | Fuel and lubricating compositions containing N-hydroxymethyl succinimides |
US4439336A (en) * | 1978-11-13 | 1984-03-27 | Ethyl Corporation | Lubricant composition containing mixed fatty acid ester and amide of diethanolamine |
US4705666A (en) * | 1983-11-12 | 1987-11-10 | Henkel Kommanditgesellschaft Auf Aktien | Alkanolamin salts of alkenyl succinic acid dialkyl semiamide corrosion inhibitors |
US5516444A (en) * | 1994-10-13 | 1996-05-14 | Exxon Chemical Patents Inc | Synergistic combinations for use in functional fluid compositions |
WO2018013527A3 (en) * | 2016-07-14 | 2018-02-15 | Chevron Oronite Company Llc | Polyester dispersants, synthesis and use thereof |
US10196343B2 (en) | 2013-01-30 | 2019-02-05 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
US10308886B2 (en) | 2015-04-22 | 2019-06-04 | Ecolab Usa Inc. | Development of a novel high temperature stable scavenger for removal of hydrogen sulfide |
US10336950B2 (en) | 2016-07-29 | 2019-07-02 | Ecolab Usa Inc. | Antifouling and hydrogen sulfide scavenging compositions and methods |
US10407626B2 (en) | 2015-09-08 | 2019-09-10 | Ecolab Usa Inc. | Hydrocarbon soluble/dispersible hemiformals as hydrogen sulfide scavengers |
US10538710B2 (en) | 2017-07-13 | 2020-01-21 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
US10584286B2 (en) | 2015-09-08 | 2020-03-10 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
US11499108B2 (en) | 2019-01-23 | 2022-11-15 | Championx Usa Inc. | Complete removal of solids during hydrogen sulfide scavenging operations using a scavenger and a Michael acceptor |
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US2588412A (en) * | 1948-09-16 | 1952-03-11 | Gulf Research Development Co | Mineral oil compositions |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US3183070A (en) * | 1961-04-28 | 1965-05-11 | Standard Oil Co | Rust inhibited oil containing aliphaticaminoalkylsuccinates |
US3368971A (en) * | 1965-11-22 | 1968-02-13 | Ethyl Corp | Lubricating oil compositions |
-
1967
- 1967-11-17 US US683774A patent/US3458444A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2588412A (en) * | 1948-09-16 | 1952-03-11 | Gulf Research Development Co | Mineral oil compositions |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US3183070A (en) * | 1961-04-28 | 1965-05-11 | Standard Oil Co | Rust inhibited oil containing aliphaticaminoalkylsuccinates |
US3368971A (en) * | 1965-11-22 | 1968-02-13 | Ethyl Corp | Lubricating oil compositions |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4081388A (en) * | 1975-04-18 | 1978-03-28 | Orogil | Compositions based on alkenylsuccinimides as additives for lubricating oils |
US4208293A (en) * | 1978-11-13 | 1980-06-17 | Ethyl Corporation | Improved crankcase lubricant composition |
US4439336A (en) * | 1978-11-13 | 1984-03-27 | Ethyl Corporation | Lubricant composition containing mixed fatty acid ester and amide of diethanolamine |
US4325827A (en) * | 1981-01-26 | 1982-04-20 | Edwin Cooper, Inc. | Fuel and lubricating compositions containing N-hydroxymethyl succinimides |
US4705666A (en) * | 1983-11-12 | 1987-11-10 | Henkel Kommanditgesellschaft Auf Aktien | Alkanolamin salts of alkenyl succinic acid dialkyl semiamide corrosion inhibitors |
US5516444A (en) * | 1994-10-13 | 1996-05-14 | Exxon Chemical Patents Inc | Synergistic combinations for use in functional fluid compositions |
US10703710B2 (en) | 2013-01-30 | 2020-07-07 | Ecolab Usa Inc. | Hydrogen sulfide scavengers |
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